Building a Strong Company Culture for an Insurance Brokerage -

Developing a strong culture from the ground up is both a challenge and an opportunity for a growing insurance brokerage. A strong culture aligned with core values (e.g. accountability, trust, client service, teamwork, integrity, innovation) will not only make the company a better place to work, but also drive client satisfaction and business performance.

Below, we outline key principles of culture-building, a step-by-step implementation plan, pitfalls to avoid, and real examples from insurance firms, along with tips on sustaining culture as the brokerage expands.

Core Principles for Building Culture

Define Clear Values and Mission: Start by articulating a set of core values and a mission that resonate with your business purpose. In insurance and financial services, values like integrity, trust, accountability, client-centric service, and teamwork are common pillars. Make these more than slogans – they should guide everyday behaviour. Studies show that workplace culture heavily influences retention (culture was found to be 10x more important than compensation in predicting turnover).

Employees are more engaged and proud when they feel the company has a clear purpose and values, and when those values are modelled consistently. For example, Deloitte’s outlook for insurers emphasises embracing a driving mission and underlying values so that employees feel pride and connection to the company’s purpose. Don’t defer defining your culture: even as a small business, explicitly answer “Why do we exist? What do we believe? Where are we going?” as early as possible. This provides “guardrails” for decision-making and reassures employees about the bigger picture, which boosts commitment and reduces turnover.
Leadership Commitment and Role Modelling: Culture starts at the top. Company leaders and managers must embody the stated values through their actions and decisions. Employees quickly notice if leadership “walks the talk” or if values are only preached but not practised. A healthy culture requires leaders to be consistent, transparent, and supportive, because about 70% of an employee’s experience of culture is driven by manager behaviour. In practice, this means if you claim to value integrity, client care, or collaboration, you promote and reward people who exemplify those traits (not just those who hit numbers at all costs).

Conversely, if a leader tolerates or rewards behaviour that undermines the values, the culture will be undermined. Successful insurance firms emphasise that leadership should listen to employees, maintain an open-door policy, and back up words with actions. For example, at one award-winning agency, employees noted that “leadership consistently backs up their words with action” in supporting staff and clients. Managers led by example by stepping in during a heavy workload period to prevent burnout and ensure clients still received top service. This kind of visible commitment builds trust. In short, leaders should treat culture-building as a strategic priority (not just an HR task) and demonstrate the values daily in how they handle clients, make decisions, and treat their team.
Trust, Autonomy, and Accountability: An atmosphere of trust is crucial for a positive culture. This means empowering employees to do their jobs without micromanagement, giving them ownership of their work, and holding everyone accountable to high standards. In a smaller brokerage (around 20 people), a “flat” organisation structure can help – minimise unnecessary hierarchy so everyone feels their voice counts. One regional insurance firm attributed its great culture to the absence of micromanagement and a feeling of autonomy: “The agency gives everyone the authority to make decisions on their own, to do the right thing without needing to consult a manual or a superior… we have a very flat organisation, with virtually no middle management”.

When people have the freedom to make decisions, it signals trust and builds accountability. To instil accountability, you can give team members clear ownership of outcomes. For instance, a larger brokerage allows each agent to own their book of business, creating a personal stake in client relationships and an “entrepreneurial spirit” of responsibility. The message is that everyone is entrusted as a guardian of the client’s needs, not just a cog in a machine. This trust should be reciprocated with accountability – set clear expectations and uphold them fairly for all. By empowering staff while expecting them to uphold the company’s standards, you create a culture where people feel respected and responsible.
Teamwork and Collaboration: Fostering a supportive, team-oriented atmosphere is especially important in a service business. Insurance work can be high-pressure and complex, so a culture of “we’re in it together” helps employees cope and excel. Encourage collaboration across roles and make it clear that helping colleagues and sharing success are valued over internal competition. Employees at one brokerage described its culture as a “strong team [with] collaboration, support, and shared successes. Employees lift each other up and celebrate wins together…everyone strives for excellence while feeling valued.” This kind of family vibe or team spirit does not happen by accident – leadership can nurture it by organising cross-functional teamwork, pairing less experienced staff with mentors, and recognising team accomplishments (not just individual achievements).

Also, ensure respectful communication is the norm: when everyone, no matter their position, is willing to pitch in and everyone’s input is respected, it cements a true team environment. Practical steps include regular team huddles or meetings where people share challenges and help each other, as well as social bonding events to build camaraderie. In a national firm, it’s beneficial to create opportunities for employees in different offices or remote locations to connect (virtual happy hours, all-hands meetings, team Slack channels, etc.) to maintain unity. A collaborative culture not only improves morale but also leads to better client service (since behind the scenes, the team coordinates smoothly on the client’s behalf).
Client-Centric Service Ethos: In an insurance brokerage, culture should reinforce that serving the client with excellence is everyone’s job – not just a slogan, but a behaviour. Make “client-first thinking” one of your cultural tenets. This means instilling pride in doing great work for clients and going the extra mile. When employees feel a sense of purpose in protecting clients’ businesses and assets, it boosts motivation. For example, a top-performing agency explicitly frames every role as being part of “the clients’ trusted advisor” team – “everyone plays a part… our guidance and year-round partnership set us apart as accessible, long-term partners who care”. By viewing client service as a shared mission, you encourage employees to support each other in meeting client needs.

Culturally, this can be reinforced by sharing client success stories in team meetings, highlighting how teamwork solved a client’s problem, and training staff on empathy and problem-solving. Additionally, ensure that when crunch times hit (e.g. a heavy renewal season or a major claims event), leadership provides backup and resources so employees can maintain service quality without burning out. Showing that the company will never compromise on client care and will support employees in delivering it sends a powerful cultural message. Over time, a client-centric culture yields trust and loyalty in your client base, which in turn feeds employee pride in their work.
Continuous Learning and Innovation: A thriving culture is one that encourages growth, development, and even innovation. In an industry undergoing technological and market changes, instil the mindset that the company is always learning and improving. Encourage employees to pursue professional development (insurance designations, new skills) and provide resources for that (training programs, mentorship, tuition support). High-performance insurance agencies often invest in their people’s growth; employees appreciate when “additional education is always available if wanted”. Building this into culture means celebrating learning – e.g. acknowledging when someone earns a new certification or shares knowledge from courses in team forums. Innovation can also be a cultural value: a signal that new ideas are welcome and that adapting to change is part of “how we do things.”

For instance, having periodic brainstorming sessions or innovation challenges can promote creative thinking in how to serve clients or streamline operations. Access to modern tools can reinforce this innovative culture; companies that provide the latest technology and encourage experimenting with new solutions tend to attract tech-savvy talent and stay ahead. One insurer found that being an early adopter of innovations (like AI-driven analytics and modern underwriting platforms) both improved service and created a “stimulating work environment” that employees appreciate. The message is that the company is forward-looking and employees can grow their skills with the company. In practice, consider embedding regular training into the workweek (Deloitte suggests making upskilling part of the weekly routine, not ad-hoc) and establishing mentorship programs. A culture of continuous improvement keeps employees engaged (especially younger professionals who crave growth opportunities) and helps the firm stay competitive.
Integrity and Ethics at the Core: In financial services, integrity is non-negotiable – it should be a foundational principle of your culture. Emphasise doing the right thing for clients, employees, and partners, even when it’s hard. A reputation for ethics builds trust internally and externally. This might involve explicit policies (e.g. a code of conduct) but, more importantly, daily decisions that demonstrate ethical standards. If “integrity” is listed as a value, show that it truly guides actions: for example, leaders must be willing to lose business or let go of a high-performing employee if integrity is at stake. A powerful illustration comes from a CEO who faced a tough call with a top performer engaged in unethical behaviour. Despite the employee’s sales results, the CEO decided to terminate him, reinforcing to the whole company that “this is a boundary you can’t cross, no matter who you are”. This sent a clear message that nobody is above the culture. Such consistency prevents a toxic environment where rule-breakers are tolerated for convenience.

To weave integrity into culture, you can incorporate ethical decision-making into training, encourage employees to speak up about concerns, and ensure transparency in communications. Also, highlight positive examples – e.g. when an employee admits a mistake and fixes it in the client’s best interest, recognise that as living the value of integrity. Over time, a culture grounded in trust and ethics will earn loyalty from clients and pride from employees. (Note: A study of the “Great Resignation” found that toxic elements like disrespect and unethical behaviour were top drivers of turnover, underscoring that integrity and respect aren’t just moral ideals but keys to retention.)
Employee Well-Being and Flexibility: Modern company culture must also value work-life balance and employee well-being. Especially with ~50 employees and possibly a mix of in-office and remote work, demonstrating care for employees’ personal and mental health will strengthen loyalty and productivity. Consider flexible work arrangements (remote or hybrid options, flex hours) to support different needs – this shows trust in employees to manage their time and has become a baseline expectation in many insurance organisations. For instance, Nationwide’s brokerage division found that offering a mix of remote, hybrid, and in-office roles catered to diverse preferences and signalled trust, resulting in a more empowered and productive workforce. Additionally, encourage employees to take their vacation and provide adequate PTO – burnout is a real risk in insurance (fast-paced, service-oriented work). High-performing agencies often have policies like generous PTO and even “floaters” or backup staff to cover for colleagues on leave, which helps people actually unplug without guilt. This kind of structural support (extra resources during crunch times, backup for those on vacation, etc.) is a strong cultural message that “we have each other’s backs.”

Also, incorporate wellness into the culture: perhaps host periodic wellness sessions, allow mental health days, or simply ensure health benefits are robust. One award-winning brokerage, for example, kept a focus on personal well-being by readily accommodating serious health situations (like extended leave during heart surgery or cancer treatment) – coworkers and leadership actively supported those individuals without pressuring them, reinforcing a culture of genuine care. Such actions build immense loyalty. In summary, treat your employees as your most important assets – if they feel supported and balanced, they will deliver great service to clients and contribute positively to the culture.

(By embedding these core principles – clear values, strong leadership, trust and accountability, teamwork, client focus, innovation and learning, integrity, and employee well-being – your brokerage will lay a solid cultural foundation. Next, we discuss how to implement these principles step by step.)

Step-by-Step Implementation Plan

1. Articulate Your Core Values and Mission (and Do It Early): Begin by defining 3–6 core values and a concise mission statement for your brokerage. Involve your founding team or early employees in this process so there’s buy-in. Be specific – for example, values might be “Accountability: We own our results and keep our promises”, “Trusted Advisors: We always put the client’s interest first”, “One Team: We support each other to succeed together”, etc. Document what each value looks like in action. Don’t just write them down and forget them: communicate them company-wide and integrate them into your onboarding from day one. As one small-business CEO advised, “Focus on your culture as early as you can…people want to know where you’re going, and why their work matters. Without a defined culture, employees get disenchanted and move on.” Make sure the values are genuine to your leadership style and business — “not just hanging on a wall” but reflected in daily decisions. This early clarity will guide hiring (hire people who resonate with these values) and set the tone for everything else.

2. Align Leadership and Set the Example: Get your leadership team (founder(s), managers) on the same page about the culture you want to build. Have explicit conversations about “what kind of company do we want to be?” and how leaders are expected to behave. Ensure leadership buy-in that culture is a top priority. Assign clear ownership for culture initiatives (e.g. the CEO or a culture champion must keep it on the agenda), but also reinforce that everyone is responsible for culture, not just HR. From day one, leaders should consistently model the values: e.g. if “transparency” is a value, practice open communication about company performance; if “community” is a value, have leaders volunteer alongside staff. This step also includes setting up some basic cultural practices: for example, institute an “open-door” or open communication policy so employees know management is approachable. Schedule regular check-ins or town halls where leadership updates the team and listens to concerns. Early on, even if informal, these habits signal the kind of culture you’re building. Essentially, leadership needs to embody the culture and make it visible – as the saying goes, “the culture of an organisation is shaped by the worst behaviour the leader is willing to tolerate.” So leaders must be ready to call out bad behaviour that conflicts with values and celebrate good behaviour that exemplifies them. This alignment at the top creates credibility for all the next steps.

3. Hire and Onboard for Cultural Fit: As you grow from the founding team to 50+ employees, hiring is your chance to shape culture intentionally. Don’t rush to fill positions with the most skilled candidates without considering their fit with your values and desired behaviours. Incorporate culture into your hiring process: for example, interview questions that probe honesty, teamwork, or client philosophy; involve multiple team members in interviews to assess fit; and explicitly communicate your values to candidates so they opt in knowingly. Many successful agencies hire for attitude and cultural alignment, then train the technical skills. As one insurance CEO put it, “Don’t hire by technical skill sets. Hire good people, then get out of their way and let them do their thing!”. That means prioritising traits like integrity, initiative, and collaboration in new hires – these people will strengthen your culture. Also, bring in diverse backgrounds that complement the team (e.g. if everyone is from one industry, consider candidates from another to avoid groupthink). Once hired, onboard new employees thoroughly into the culture: have a welcome program that goes beyond job training to introduce them to the company’s story, values, and expectations. Pair each new hire with a mentor or “buddy” who exemplifies the culture, so they learn not just the tasks but “how we do things here” by example. Early investment in acculturating employees will pay off in them embracing and propagating the desired behaviours.

4. Embed Cultural Values into Policies and Practices: Ensure that your day-to-day business practices and HR policies reinforce the culture you want, rather than contradict it. This step is about integrating values into the “operating system” of the company. For example, if teamwork and knowledge-sharing are values, set up regular team meetings or collaboration tools, and perhaps avoid commission structures that are 100% individual with no team component. If accountability is a value, implement goal-setting and review processes that hold people to their commitments (for instance, quarterly OKRs or performance check-ins explicitly tied to both results and living the values). Document behavioural expectations in an employee handbook or culture guide that includes scenarios of value-aligned behaviour. You might also create a culture committee or assign culture ambassadors – employees from different departments who plan team-building activities or surface issues. As your brokerage is small, even informal practices can reinforce culture: e.g. institute a policy that everyone, regardless of title, helps answer phones for a couple of hours during peak periods – signalling that no task is beneath anyone and clients come first. “What gets rewarded gets repeated,” so design your recognition and compensation systems to reward not only sales numbers but also teamwork, customer service excellence, and innovation. Some firms, for instance, give “culture awards” or shout-outs in company meetings (more on recognition in the next step). Also, align any corporate policies with your values: a simple example, if “trust” is a value, you might have a flexible work-from-home policy rather than rigid clock-in rules. Or if “learning” is a value, offer reimbursement for continuing education. By baking values into the company’s processes (hiring, onboarding, meetings, evaluations, etc.), you make it far more likely that the stated culture becomes the lived culture.

5. Encourage Open Communication and Continuous Feedback: Build mechanisms for two-way communication so that employees feel heard and included in shaping the workplace. Culturally, this fosters trust and continuous improvement. Concretely, you can schedule regular one-on-one meetings between managers and their team members to discuss not just work tasks but how things are going in general. Hold periodic all-hands meetings or luncheons where leadership updates the company on progress and invites Q&A. It’s also wise to use anonymous surveys or feedback tools (perhaps every 6 or 12 months) to gauge employee sentiment on culture, gather suggestions, and spot issues early. Research indicates that employee surveys can help identify patterns and build a more inclusive, engaging culture if acted upon. When you get feedback, act on it where possible (even small changes, like adjusting a policy based on employee input, show that speaking up leads to results). This will reinforce a culture of transparency and improvement. Additionally, maintain clear internal communication channels – whether that’s an intranet, a chat platform like Teams/Slack, or even a monthly internal newsletter highlighting cultural initiatives and kudos. In a national brokerage, keeping everyone connected is vital to avoid silos. Effective communication practices ensure that even as you grow, people feel they know what’s happening and can voice concerns or ideas safely. A culture with high psychological safety (where people can express themselves without fear) will be more innovative and resilient. Leaders should model this openness: share bad news as well as good, admit mistakes, and invite dialogue. Over time, this step builds trust and engagement, as employees see that the company values their voice.

6. Recognise and Reinforce Desired Behaviours Consistently: Positive reinforcement is one of the strongest tools to shape culture. Make it a habit to recognise employees who exemplify the company values and deliver great work. This can be formal (e.g. an “Employee of the Month” who lives the values, with a small reward) and informal (shout-outs in meetings, a thank-you email copied to the team, peer-nominated kudos, etc.). Especially for a small company, these gestures have big impact – they signal to everyone “this is what we applaud around here.” In insurance agencies, where work can be routine or stressful, frequent recognition boosts morale and engagement. In fact, industry experts recommend making recognition a routine part of the workflow (not a rare event). Consider implementing peer-to-peer recognition: for instance, allow team members to publicly praise a colleague each week for something (hitting a customer service milestone, helping on a tough project, etc.). Some firms use digital social platforms for this purpose, but even a shared email thread or a Slack channel for kudos can work. The key is authenticity – the praise should be meaningful and tied to specific actions or results. “When recognition happens often and feels genuine, it becomes part of the team’s rhythm” in a positive culture. It creates a virtuous cycle: employees feel valued and motivated to repeat those positive behaviours. Also, celebrate team successes: landed a big client? Exceed a quarterly goal? Take time to celebrate as a group (a team lunch or virtual celebration) to reinforce that success is appreciated. This ties back to values as well; for example, if a team came together to solve a client’s complex claim, celebrate both the outcome and the collaborative way it was achieved. Alongside recognition, ensure you support career growth as a reward for cultural alignment. Employees who contribute to the culture and improve their skills should see a path for advancement or new opportunities. Whether it’s promotions, leadership of a new project, or simply gaining new responsibilities, career development is a form of recognition that shows the company invests in its people. Providing clear pathways and training for those who seek growth will reinforce a culture of continuous learning and achievement. All these reinforcement steps sustain momentum so that the desired culture doesn’t fade after an initial push – it becomes ingrained in everyday life at the company.

By following these implementation steps – from defining values early, to aligning leadership, hiring thoughtfully, embedding values in processes, keeping communication open, and continuously recognising good work – a new brokerage can deliberately craft a strong culture rather than leaving it to chance. Next, we’ll look at common pitfalls to watch out for on this journey.

Common Pitfalls to Avoid

Even well-intentioned culture initiatives can go awry. Below are some common pitfalls that leadership should be mindful of, to avoid when building and maintaining the company culture:

Hollow or Hypocritical Values: One of the biggest mistakes is to declare inspiring core values, but then not live by them in practice. Values that are just words on a website or posters on the wall – without genuine commitment – will breed employee cynicism. For example, if you say “Integrity” is a value but tolerate cutting corners for a quick sale, employees will conclude the real culture is “growth at any cost.” Avoid aspirational platitudes that you can’t operationalise. Instead, choose values you’re ready to enforce, and prove your commitment through actions (especially when it’s difficult). As Harvard researchers note, defining values without real follow-through makes them “inauthentic and hollow — and employees know it.” If your brokerage’s values include respect, integrity, teamwork, etc., leaders must exemplify those daily. Consistency is key: misalignment between stated values and actual behaviours (even just one high-profile contradiction) can quickly erode trust in leadership.
“Do as I Say, Not as I Do” Leadership: This relates to the above pitfall but is worth emphasising. If managers or executives violate the cultural norms (e.g. a leader talks about accountability but frequently blames others, or preaches work-life balance but then praises 80-hour work weeks), it undermines the entire culture effort. Employees take cues from the top; toxic work cultures often stem from toxic leadership behaviours. Inaction on bad behaviour is also a leadership failure – ignoring problems like harassment, unethical conduct, or favouritism sends a message that those behaviours are acceptable. To avoid this, hold leaders and high performers to the same standards as everyone else. A critical (and hard) test is when a star salesperson or key executive behaves in ways that violate the culture. If leadership gives them a pass because of their results, the culture of integrity or respect is effectively broken. As Wharton’s Gad Allon advises, who you promote or fire based on behavior sets the cultural tone more than any slogan. A strong culture sometimes requires making an example by removing even a top performer who is toxic or dishonest. It’s better to lose one person than lose the trust of the whole team. Leaders should remember that everyone is watching their choices closely for signals of “what really matters here.”
Overemphasis on Perks or Superficial Indicators: Beer on Fridays, a ping-pong table, or free snacks can be nice perks, but don’t mistake those for culture. Small companies sometimes think they need flashy Silicon Valley-style perks to seem like they have a cool culture, but culture runs deeper. Focus on substance (values, behaviour, trust, growth) over symbols. As one entrepreneur put it, “The perks…will carry you for a while, but ultimately people want to know why they’re doing the work they’re doing.” Likewise, spending a lot of time crafting a beautifully worded mission statement or decorating the office is not sufficient if daily experiences don’t match it. Avoid culture theatre – things that look good on the surface but aren’t backed by genuine policy or practice. For instance, touting “we’re like family” in recruiting materials, but then having inflexible rules that ignore individual needs, will ring false. It’s a pitfall to believe morale can be bought with gimmicks; employees see through that. Invest in meaningful benefits and an environment of respect before worrying about trendy extras. In short, don’t confuse perks with culture – a game room is nice-to-have, but a supportive manager is need-to-have.
Neglecting Employee Growth and Career Pathways: Many small businesses get busy with day-to-day operations and forget that employees (especially ambitious or younger ones) need to see a future for themselves. If there’s no clear development path, training, or advancement, top talent may leave even if the immediate environment is friendly. Culture is not just about fun and camaraderie; it’s also about professional fulfilment. Avoid a pitfall of culture becoming “stagnant” – where people feel stuck. High-performing agencies keep talent engaged by offering mentorship, education, and promotions from within. If you ignore this, you risk turnover. Periodically ask employees about their career goals and help map out opportunities (new roles, certifications, leadership chances). An “always learn” culture keeps your team motivated and loyal. Conversely, a culture that doesn’t reward ambition or innovation can become complacent and fail to attract new talent.
Poor Communication and Lack of Transparency: Secrecy or unclear communication from management can quickly poison culture. When employees feel decisions are made behind closed doors and information is withheld (especially on matters like company performance, changes, or crises), it breeds distrust and rumours. One expert noted that “a lack of transparency… opens up a vacuum for gossip and conspiracy theories”, which, once started, are hard to dispel. The pitfall here is thinking that you should only share information on a “need-to-know” basis or sugarcoat bad news. In reality, most people prefer honesty. If times are tough or mistakes happen, say so directly – employees will respect straight talk and rally better than if they suspect they’re being misled. Also, ensure managers provide regular feedback; a culture where feedback only comes during annual reviews (or only when negative) can feel unsupportive. Keep communication channels open, encourage questions, and respond to concerns promptly. Without this, small issues fester and trust erodes. Avoid the mistake of thinking “no news is good news” – in a culture vacuum, employees often assume the worst. Proactively share updates and the reasoning behind decisions. Leaders who communicate openly, even about challenges, foster a culture of mutual respect and confidence.
Micromanagement and Lack of Trust in Employees: If your culture slides into one where every decision requires high-level approval, managers second-guess team members, or employees are afraid to take initiative, you have a trust problem. Micromanagement not only slows down work but also signals to employees that they aren’t trusted or competent. This can kill morale and innovation. Avoid managers who hover or overly control how work is done – instead, train leaders to empower their teams, give clear goals, then step back. A pitfall for new entrepreneurs is having trouble delegating (since the company is your “baby”), but failing to delegate undermines the culture you want. Talented employees will chafe if they have no autonomy. The example from Cleary Insurance is instructive: they credit their flat, no-micromanagement structure for employees’ happiness and success. On the flip side, a toxic sign is when employees feel surveilled or not allowed to make any decision. Strive to push decision-making down to the lowest reasonable level. Trust also means not penalising people for appropriate risk-taking or honest mistakes – if folks fear blame, they won’t take initiative. In summary, avoid building a culture of control; build one of empowerment with accountability.
Tolerating “Brilliant Jerks” or Ethical Lapses: We touched on this under leadership, but to be clear: making exceptions for high performers who behave poorly is a recipe for cultural ruin. If an employee brings in a lot of revenue but bullies colleagues or violates rules, the short-term gain will be outweighed by long-term damage (others disengaging or leaving, and a precedent that values don’t matter). Some companies fall into the trap of “results at all costs,” rewarding toxic rainmakers. This creates what MIT researchers call a toxic culture – one with unethical behaviour or lack of respect – which has been strongly linked to high turnover. To avoid this, define unacceptable behaviours (e.g. dishonesty, harassment, disrespect) and enforce consequences consistently. As painful as it might be to discipline or fire a top salesperson, doing so can save your culture and ultimately your business. The Wharton case study of the CEO who fired a star employee for an integrity breach is a prime example: it sent a clear cultural message that integrity truly is inviolable at that company. Also, be cautious not to inadvertently create a culture of hero worship around a few “indispensable” individuals – that can lead to those people feeling above the rules. Make it known that no one is above the culture.
Ignoring Diversity, Equity, and Inclusion (DEI): Another pitfall is neglecting to foster an inclusive environment, especially as you grow. A culture will stagnate if only one type of person thrives. Lack of diversity and inclusion can manifest as cliques, “in-group vs out-group” dynamics, or even discrimination – all toxic to a healthy workplace. Insurance may historically be male- or one-ethnicity-dominated at leadership levels, but to attract modern talent, you should prioritise inclusion. This means ensuring hiring and promotions are fair, creating space for different voices (inviting input from junior staff, for example), and educating the team on respectful behaviour. Not addressing off-colour jokes or unconscious bias is a mistake; it alienates people and harms collaboration. On the positive side, embracing DEI can become a strength – diverse teams often bring in wider perspectives and serve clients better. So avoid the trap of cultural homogeneity. Every employee should feel respected and that they belong (any signs of exclusion should be dealt with swiftly). The best agencies often highlight that “everyone is respected and valued” in their culture. Make that a non-negotiable.
Failing to Evolve as You Scale: Culture isn’t set in stone – it needs care and adjustment as the company grows or circumstances change. A pitfall is thinking “we defined our culture once, we’re done.” For instance, a tight-knit culture when you were 10 people in one office will need adaptation when you’re 50 people across several locations. If leadership doesn’t proactively scale communication, traditions, and policies, the culture can dilute. Don’t become complacent; regularly revisit if your practices still serve the values. Solicit feedback: what worked for 10 people may not work for 50. Another aspect is external changes – e.g. the shift to remote work in 2020 forced cultural adaptations (more intentional check-ins, flexibility, new tools). Companies that resisted change and tried to enforce old norms suffered. Avoid rigidity; uphold core values but be open to new ways to express them. For example, if teamwork is a value, pre-pandemic it might have been demonstrated by in-person huddles; now it could mean daily Zoom stand-ups or collaborative software. If continuous improvement is part of your culture, you should apply that to the culture itself, too. A healthy culture has feedback loops to correct course (more on sustaining culture in the next section). By staying vigilant and adaptive, you’ll prevent the culture from “drifting” or deteriorating as you expand.

In summary, be on guard for these pitfalls: saying one thing but doing another, relying on fluff over substance, letting poor behaviour slide, and not listening to your employees. Avoiding these will help ensure your culture-building efforts actually take root and last.

Case Studies or Examples from Brokerage Businesses

It can be helpful to see how other insurance and service-oriented companies have successfully built strong cultures. Here are a few real-world examples and the lessons they offer:

Robertson Ryan Insurance (RRI) – Balancing Growth with a “Small Company” Feel: Robertson Ryan is a U.S. brokerage that has grown over 60 years from a handful of people to over 150 agents (and hundreds more support staff) nationwide. Despite its size, RRI has maintained a close-knit, supportive culture – a result of very intentional efforts by leadership. They operate with the philosophy of “being big, yet acting small”, meaning they have resources of a larger firm but strive for personal touches in how they treat employees. At RRI, employees consistently report feeling valued, heard, and supported by management. The company encourages a flexible work culture (offering remote, hybrid, and in-office options to fit individual needs) and generous benefits like ample PTO and profit-sharing. This flexibility stems from leadership’s belief that a happy, balanced workforce is more productive – reflecting a high level of trust in employees to manage their work and life. RRI has also institutionalised its culture through structures like an Employee Engagement Committee (which plans team events and initiatives) and a Charitable Foundation (involving staff in community giving). These programs are “woven into [the] daily operations” rather than afterthoughts, reinforcing engagement and a sense of purpose. Crucially, RRI’s leadership shows consistency between words and deeds. In one instance, when the team faced an “unusually heavy renewal season,” leadership proactively stepped in – they provided extra staff help (a “floater” support team), allowed flexible scheduling, and even personally assisted, to ensure no one felt overwhelmed and every client still received top service. Employees took note of this and cited it as proof that management truly cares and lives up to the value of supporting both employees and clients. RRI’s Senior VP Allan Degner summed up their approach: “We’ve been intentional about building a culture that thrives on flexibility, engagement, recognition, and support… these commitments are part of our identity.”. The results speak for themselves – RRI has won “Best Place to Work” awards repeatedly, and enjoys low turnover and high employee referral rates. The takeaway for a smaller brokerage is that even as you grow, you can preserve a strong culture by investing in employee well-being, keeping communication personal, and making sure leadership decisions consistently reflect the espoused values.
Cleary Insurance – Family Atmosphere and Trust in Employees: Cleary Insurance is a Boston-based independent insurance agency with a staff size closer to the user’s brokerage (on the order of a few dozen employees). Cleary has cultivated a “supportive, family atmosphere” over the years, which was recognised when it won a regional Best Agency to Work For award. Employees describe Cleary’s culture as one that “fosters both professional growth and personal fulfilment,” built on collaboration and mutual support. A standout aspect of Cleary’s culture is the high level of trust and autonomy given to team members. The agency operates with virtually no middle management; instead, leadership empowers every employee to “make decisions on their own [and] do the right thing” without needing constant approval. This flat structure means people feel trusted to use their judgment, which boosts their confidence and morale. It also promotes accountability – team members understand they own their decisions. The respect is mutual: no matter someone’s position, colleagues are willing to roll up their sleeves and help each other, creating a true team environment where “everyone is respected”. Another hallmark of Cleary’s culture is genuine care for employee well-being (akin to a family taking care of its own). For example, when an employee faced a serious health issue (heart surgery), the company provided extensive support – helping with disability benefits, adjusting her workload, and ensuring her job was secure until she could return. In another case, an employee undergoing cancer treatment was kept on payroll and not pressured about returning, with the president personally checking on her and assuring her “we have your back”. These stories spread internally and reinforce enormous loyalty and a sense of safety among staff. Cleary also stays competitive with compensation (cost-of-living raises, profit-sharing, fair bonuses), but employees there often emphasise the healthy working environment over pay alone. The firm involves employees in finding new hires as well – because the team is so invested in the positive culture, they actively refer friends who would fit in. Leadership at Cleary (the owner, Bill Cleary, and his VP) lead by example, keeping an open-door policy and working as hard as anyone. They make culture a continuous effort, always asking how they can “do better for employees and clients.” The success of Cleary Insurance illustrates that a smaller brokerage can create a loyal, high-performing team by treating people like family, entrusting them with responsibility, supporting them in and out of work, and hiring folks who embrace those values. Trust and empathy, combined with a drive for excellence, made Cleary both a great place to work and a great service provider for clients.
The Liberty Company Insurance Brokers – Culture as a Growth Engine: The Liberty Company is a national brokerage (with multiple offices) known for its strong emphasis on culture. CEO Bill Johnson describes their culture as “a unique and ever-evolving blend of our values: teamwork, kindness, good feelings, fun, integrity, fairness, excellence, and caring”. Importantly, he stresses that it’s not just a list on paper or marketing copy, but “the heartbeat of our organisation” that guides all actions. Liberty’s leadership consciously prioritises culture even as they expand through acquisitions and rapid growth. For instance, Johnson notes that when making decisions about raising capital or partnerships, they weigh short-term financial gains against effects on culture, often foregoing options that would damage their values. Integrity is non-negotiable in these choices, which in the long run “strengthens our reputation and solidifies trust”. Liberty also invests heavily in employee wellness and personal growth, seeing these as key to culture. They have initiatives like mindfulness and meditation sessions led by a Chief Wellness Officer, and “Talks” with health and wellness thought leaders open to employees, clients, and industry peers. This focus on caring for employees’ mental and physical health creates an environment where people feel supported to do their best work (and is aligned with their mission of providing “Peace of Mind with Great Care” to clients). Additionally, Liberty monitors and nurtures its culture through multiple strategies: continuous Learning & Development programs (including leadership, diversity and inclusion, and personal growth topics), and regularly seeking feedback to ensure alignment with values. As Johnson puts it, their culture “empowers us to make a difference in the lives of our clients and communities… fueling our growth”. The Liberty Company’s example shows that scaling up doesn’t require diluting culture – if anything, you can double down on it. By clearly defining a broad set of human-centered values and treating culture as the cornerstone of strategy, they attract like-minded talent and differentiate in the marketplace. A takeaway here is to be explicit and passionate about your cultural values and use them as a north star in decision-making. Also, don’t be afraid to infuse some fun and positivity (one of Liberty’s values is “good feelings/fun”) – a joyful workplace can be compatible with high performance.
Adjacent Example – A Tech-Enabled Insurance Startup: It’s worth noting an adjacent example outside traditional agencies: Newfront Insurance, a tech-driven brokerage startup, grew rapidly by blending Silicon Valley culture elements with insurance expertise. Newfront focused on creating a culture of innovation, data-driven decision-making, and employee empowerment, which helped it attract top talent from both tech and insurance fields. They emphasised modernising the insurance brokerage experience (for both clients and employees) by using technology, which became a point of pride internally. One lesson from Newfront is the importance of a learning culture – they invested in training their team on new digital tools and encouraged open-minded experimentation. They also maintained a client-first ethos to avoid the trap of “tech for tech’s sake.” While a small startup, Newfront ensured frequent all-hands meetings and transparent communication to unite everyone around the mission of transforming the industry. For a new brokerage, the Newfront case underscores that you can differentiate your culture by embracing innovation and agility, as long as you keep it tied to delivering better client service. It’s an example of how culture can be a competitive advantage – in their case, attracting entrepreneurial employees who wanted to shake up the status quo in insurance.

Each of these examples – whether a longstanding firm like RRI, a boutique agency like Cleary, or an expansive broker like Liberty – reinforces core lessons. Listening to employees, trusting them, investing in their growth and well-being, and aligning business decisions with cultural values are strategies that yield engaged teams and satisfied clients. They also show that culture is not a one-time project but an ongoing commitment from leadership. As your own brokerage implements its culture, borrowing these best practices and tailoring them to your context will help you replicate their success in building a great place to work and do business.

Tips for Sustaining Culture at Scale

Building a positive culture is an important first step – but sustaining it as your brokerage grows is the real challenge. Culture can evolve or erode over time if not actively managed. Here are practical tips to keep your culture strong and intentional as you scale up:

Hire, Promote, and Reward in Line with Values: The most powerful levers for maintaining culture are who enters, rises in, or exits your organisation. As Wharton’s research highlights, “who you hire, who you promote, and who you fire” tells everyone what your company truly values. To sustain your culture, be relentless in recruiting people who fit and enrich your values (skills can be taught, attitude can’t). Likewise, promotions should go to those who not only perform well but also embody the culture and elevate others. When employees see that cultural leadership is a criterion for advancement, they’ll emulate those behaviours. Conversely, if someone – even a top salesperson – undermines the culture (toxic behaviour or ethical lapses), deal with it decisively. Removing or correcting cultural misfits sends a clear message that you mean what you say. This consistency will preserve the integrity of your culture over time. As you expand, consider formalising culture-fit interviews and 360-degree feedback in performance reviews to ensure decisions align with your values. By making cultural alignment a key part of HR decisions, you essentially “bake in” the culture for the long term.
Keep Communication and Connection Scalable: A tight culture often comes from the camaraderie of a small team. To sustain that as you grow to multiple teams or offices, intentional communication routines are vital. Continue (or start) regular all-company meetings or video calls to share updates and celebrate wins, so everyone hears the same message from leadership. Encourage cross-location collaboration – for example, have project teams with members from different offices or rotate who attends certain leadership meetings, to prevent silos. Setting up company-wide communication channels (like an intranet, Slack, Teams etc.) where people can interact casually and professionally helps maintain a sense of community beyond physical proximity. One best practice is to establish recurring touchpoints: weekly team check-ins, monthly virtual social events, quarterly town halls, annual off-sites, etc. These create rhythms that bind employees together. As one expert noted, when teams are far-flung, creating “meaningful touchpoints… that make everyone feel seen and valued – no matter where they’re logging in from – is key”. For example, you might implement a weekly “virtual coffee chat” pairing employees at random to chat and get to know each other, strengthening interpersonal bonds. Leverage technology to bridge distances: use video meetings rather than just phone calls, and consider tools like internal social networks or recognition platforms that make cultural sharing easy. The goal is to ensure that as headcount increases, employees still feel connected to the leadership and to colleagues across the organisation, preserving that family/team feeling from the early days. A culture of open communication and camaraderie can scale if you deliberately provide avenues for interaction at scale.
Scale Traditions and Rituals (but Also Adapt Them): The little cultural rituals that worked with 10–50 people (like Friday team lunches or shout-outs in morning huddles) might need to be evolved for 100 people, but don’t abandon them entirely. Instead, find ways to scale up your cultural rituals or create new ones that fit the larger size. For instance, if you used to celebrate each employee’s birthday with a cake in the office, at 100+ people that could be too frequent – but you could switch to a monthly birthday celebration or a digital kudos board for birthdays. If you always did an annual “insurance olympics” competition for team-building, continue it as you grow, just split people into more teams. These shared experiences, even if adjusted, help carry forward the culture’s personality. Many companies institutionalise important elements by creating committees or assigning owners: e.g. a Culture or Engagement Committee with members from different departments can ensure events and initiatives keep happening as the company grows (RRI did this with their Employee Engagement Committee to keep employees involved in culture decisions). Documenting your origin story and past cultural moments can also help newcomers feel part of the legacy. However, also be open to new traditions that fit a bigger organisation or a more diverse workforce – maybe as you expand, employees suggest new activities (like a volunteering day, hackathon, or wellness challenge) that can become part of your culture. Embrace these, as they keep the culture dynamic and inclusive of new people’s ideas.
Maintain Leadership Accessibility and Listening: In a small firm, the founder might chat with every employee daily. At larger scale, that intimacy can fade, but you can take steps to remain an approachable leadership team. Continue practices like skip-level meetings (where higher managers periodically meet junior employees directly), Q&A sessions in town halls, and encouraging employees to email or message ideas to leadership. Preserve an open-door ethos even if the literal door can’t always be open – for example, the CEO might hold “office hours” where any employee can book a short meeting to share thoughts. When people feel they can still reach leadership and be heard, it prevents the “big company” syndrome of disengagement. Also, keep listening mechanisms strong: use employee engagement surveys as you grow to catch any shifts in morale or values alignment. For instance, if survey feedback shows that newer hires feel less connected, you can take action (maybe pair newer and veteran employees in projects or mentoring). By actively measuring and listening, you can catch cultural drifts early. In essence, scale should not mean silence from leadership – keep up transparent, frequent communication. Many successful growing companies actually increase communication during high growth to ensure everyone stays aligned. Make sure your employees always know the company’s strategic direction and how their work contributes to it, so that sense of purpose remains strong even as org charts get more complex.
Invest in Systems that Reinforce Culture: As you get larger, informal management of culture might give way to more formal systems – which isn’t bad if done right. Consider implementing tools or programs that help manage and propagate culture. For instance, recognition platforms (software where peers and managers can give public kudos) can amplify your recognition efforts at scale. They ensure no good deed goes unnoticed, just because the team grew. Pulse survey tools can help regularly gauge sentiment. Learning management systems can support continuous development opportunities for all staff, keeping the learning culture alive. Even data analytics can assist: some platforms provide insights into engagement levels, helping you pinpoint teams that might be feeling disconnected. One caution is not to rely on tools alone – combine technology with human touch. But smart use of systems can provide consistency. For example, having an established onboarding program/workshop for new hires at scale ensures everyone gets a dose of culture education in their first week (when you were 5 people, onboarding was just sitting next to the founder; at 100 people, you need a structured program). Similarly, a mentorship or “buddy” program for new joiners can be formalised so that each person is welcomed and integrated the same supportive way you did in the early days. As Liberty Company did, continue to evolve L&D offerings and wellness programs at all levels as you grow – this maintains a focus on people’s growth and well-being at scale. The key is to proactively build infrastructure that supports your culture, rather than letting growth happen haphazardly. If you invest in these systems, employees will feel the culture is not just nostalgia from when the company was small, but a living, organised part of the larger company.
Protect Core Values During Change or Pressure: Growth phases or big changes (e.g. a merger, rapid hiring, or a sudden shift to remote work) will test your culture. It’s crucial in these moments to double down on core values and “walk the talk.” For instance, if you merge with another firm or open a new office, immediately communicate your cultural values to the new team and model them. Engage culture ambassadors in training any acquired employees on “how we do things.” If market pressures hit (say there’s a financial downturn or simply the crunch of high workload), be careful not to abandon cultural principles in a panic. For example, if “work-life balance” is a value, don’t suddenly celebrate all-nighters to meet a target – instead, openly acknowledge the pressure and perhaps all pitch in or reprioritise, so no one person is overstressed. A classic scenario is the “brilliant jerk” dilemma we discussed – often triggered by pressure to hit numbers. Under stress, some companies might be tempted to excuse bad behaviour from a top producer. Resist this; sustaining culture means holding the line on values especially when it’s hard. As one expert said, success itself can pressure culture: “when you’re very successful… you’re afraid to let go of a few people who have a lot of impact on growth. If you keep someone despite toxic behaviour because you can’t ‘jeopardise success,’ the message will be clear” (and harmful). The advice is to be steadfast that “how we succeed matters as much as success.” If leadership visibly makes a values-based decision (like parting ways with an unethical client or employee), take the time to explain it to staff – it will become a legendary story that reinforces culture for years.
Foster Community and Belonging as You Grow: When you’re 50 employees, you might all know each other’s families; at 200 employees, not so much. To sustain the sense of community, implement initiatives that help maintain personal connections and a feeling of belonging. This could include continuing company-wide volunteer or charity events (perhaps easier to do as separate regional volunteer days once you’re larger, but then share stories and photos company-wide). Community service is a great equaliser and morale boost – many firms find it unites people and renews a collective sense of purpose beyond work. It aligns with the insurance industry’s ethos of helping people. For example, Nationwide involves employees in volunteer work focusing on key impact areas, giving them paid time to participate and having leaders join in – this strengthened their culture of personal fulfilment and community connection. You can emulate this by instituting an annual “Day of Service” or supporting causes your team cares about. It’s a scalable way to keep people connected and proud of the company’s social values. Also, as new people join, ensure inclusive social practices – e.g. if you used to all go out for drinks, now you might need to invite widely or have department mixers so newcomers integrate. Consider creating affinity or interest groups (like a young professionals group, a women in insurance group, sports teams, etc.) to help employees form bonds in a larger organisation. These kinds of networks give a big company a small community feel. The broader point is to be deliberate in nurturing the “human” side of the workplace as you grow – don’t let people become just names on an org chart. A sustained culture at scale often results from many of these small community-building tactics that together preserve the soul of the company.
Periodically Reassess and Refresh Cultural Programs: Finally, realise that sustaining culture is an ongoing process. Schedule periodic check-ins on the health of your culture – perhaps an annual culture survey or a review by the leadership team asking “what’s going well in our culture, what’s slipping, what new challenges do we face?” Use data (turnover rates, survey results, etc.) to inform this. For example, if you see a rise in turnover in a particular office or team, investigate if there’s a cultural issue (lack of mentorship, a misaligned manager, etc.). Keep an eye on cultural integration if expanding via acquisitions – acquired teams need special attention to feel part of the new culture. Be willing to adjust your initiatives: maybe your initial mentorship program needs tweaking after you hit 100 employees, or your recognition program needs new categories as roles diversify. Solicit ideas from employees (the culture committee can help with this). High-growth companies often do a mid-course correction to ensure the culture evolves positively. The goal is to remain true to your core values while updating the expression of those values to fit current realities. Think of it like tending a garden – you’ll need to prune, water, and sometimes plant new seeds. By treating culture as something you continually cultivate, you’ll prevent the entropy that can set in over years. Organisations that last decades inevitably have to renew their culture to keep it vibrant and relevant (while never losing sight of the foundational principles).

In conclusion, sustaining a strong culture at scale requires constant, proactive effort. It’s about aligning your people practices with your values at every growth stage, keeping communication candid and frequent, and never becoming complacent. The reward is enormous: a cohesive culture will help your brokerage navigate growth, retain the talent that got you there, attract new talent who are excited about your ethos, and deliver consistent, high-quality service to clients even as the business expands.

Good luck on your culture-building journey! And if you need help while at it, I’m here to help.