Mentorship Is One of Insurance’s Best Answers to the Talent Gap

The insurance industry has spent years talking about the talent gap: experienced professionals are retiring, organizations are competing for emerging talent, and early-career employees are trying to build careers in an industry they may not have intentionally chosen.

Recruiting more people into insurance matters. But getting them through the door is only part of the challenge. The industry also has to help them see a future here.

That is where mentorship can make a measurable difference.

Mentorship gives professionals access to something no job description, onboarding checklist, or online course can fully replicate: perspective from someone who has already navigated the questions, decisions, and career transitions ahead of them. It helps make a large and sometimes complicated industry feel more understandable, more connected, and more human.

How the RISE Mentorship Program Has Grown

Mentorship has been central to RISE from the beginning. What started as a way to create meaningful connections between emerging and established insurance professionals has grown into a structured program serving people across companies, specialties, locations, and career stages.

As the program has expanded, the goal has remained the same: create relationships that help people grow.

For a student or early-career professional, that may mean understanding the different paths available in insurance or learning how to speak up with more confidence. For someone further into their career, it may mean preparing for leadership, navigating a transition, or gaining perspective from outside their own organization.

The growth of the program reflects a need we continue to see across the industry. Professionals want career guidance, but they may not have access to the right mentor within their company. Others are looking for a confidential outside perspective, a broader network, or insight into a role or part of the industry they have not yet experienced.

RISE helps bridge those gaps.

Mentorship as a Solution to the Insurance Talent Gap

The talent gap is often framed as a pipeline problem. In reality, it is also a development and retention problem.

People are more likely to stay and grow in an industry when they understand their opportunities, feel connected to others, and can picture what their next step might look like. A mentor can help provide all three.

Mentorship also supports one of the insurance industry’s most urgent needs: knowledge transfer. Experienced professionals carry years of context that cannot always be captured in a manual. Through mentorship, they can share lessons about decision-making, relationships, leadership, communication, and the realities of building a long-term career in insurance.

At the same time, mentorship is not a one-way transfer of knowledge. Mentors gain exposure to new perspectives, workplace expectations, technologies, and challenges affecting the next generation. The relationship gives both participants a clearer view of the industry and the people shaping its future.

That exchange builds stronger professionals and, ultimately, a stronger talent pipeline.

Alison Norris, a commercial lines underwriter at Berkley Mid-Atlantic and RISE mentor, understands that need personally. Without formal mentors early in her own nontraditional career, she had to find her way from customer service and account management into underwriting. She became a mentor because she wanted to offer someone else the resource she did not have.

“I want to help others get to that place faster,” Alison shared. For an industry facing a talent shortage, that is an important part of the solution: helping people recognize the opportunities in front of them and giving them support as they build the skills and confidence to pursue those opportunities.

What We Have Seen Come From the Right Match

The most meaningful outcomes are not always dramatic announcements. Often, they show up in the decisions participants feel better equipped to make.

RISE mentees have gained greater clarity about their career paths, expanded their networks beyond their own organizations, strengthened their confidence, and found trusted people they can turn to for honest guidance. Mentors have had the opportunity to invest in the industry’s future while sharpening their own leadership and listening skills.

Elizabeth Skertic experienced that kind of clarity as a RISE mentee. While balancing leadership, three young children, and questions about what should come next, her mentor, Steve Wang, helped her recognize that growth did not have to mean immediately pursuing another title. She chose to invest in her team, build confidence in her leadership, and look for ways to make a broader impact in her current role. That growth ultimately created an opportunity for her to advance within her own area.

Her takeaway was simple: “Having someone in your corner does not change your destination, but it can help you keep going long enough to get there.” Elizabeth has now returned to the program as a mentor herself, turning one successful match into another opportunity for knowledge and encouragement to move through the industry.

The relationship between RISE mentor Jordann Reis, Director of Growth and Client Engagement at Tyson & Mendes, and her mentee Liz Westerfield offers another example of what can happen when the right match is paired with real commitment from both people.

Reflecting on the experience, they credited both the structure of the program and their willingness to take it seriously. They completed the exercises, came prepared for their conversations, and, as they put it, “both showed up.” That consistency gave the relationship room to move beyond surface-level career advice. Liz said Jordann created a safe space where she could be vulnerable about unfamiliar or difficult situations, and their conversations helped her build confidence both professionally and personally.

The two talked about confidence in unfamiliar rooms, leadership as an ongoing process of becoming, and finding joy in continuing to learn. By the end of their formal mentorship, neither viewed the relationship as finished. Their experience captures what RISE hopes to create through each pairing: not a transactional introduction, but a relationship built through preparation, trust, vulnerability, and mutual investment.

We have also seen relationships continue beyond the formal program. Nicole Preston, Director of Client Experience at FOCUS, described her RISE mentee as a great match and said the two still communicate and check in with one another. For her, the relationship that remained after the program was the most meaningful outcome.

Luis D’Amire, Director of Learning and Development for Hudson Insurance Group, has seen similar long-term impact. He remains connected with former mentees and has watched them grow, move into new roles, navigate personal milestones, and build confidence. As Luis explained, the outcome is not always a promotion. Sometimes it is a person feeling more prepared to handle a difficult conversation, set a boundary, ask for feedback, or decide whether to pursue a new opportunity.

That matters. A successful mentorship is not simply a series of completed meetings; it is a connection that remains valuable when a new opportunity, difficult conversation, or unexpected career decision arises.

Those outcomes do not happen automatically. They begin with a thoughtful match.

The Work Behind Every RISE Mentorship Pairing

Matching mentors and mentees is much more involved than pairing two people based on a job title.

RISE considers each participant’s career stage, experience, goals, interests, area of the industry, gender, time zone, and what they hope to gain or contribute. The process also looks for alignment in communication preferences and the kinds of challenges a mentee wants help navigating. Sometimes the best match offers direct experience in the mentee’s desired path. Other times, the greatest value comes from a mentor who can offer a different perspective or open a window into another part of the industry.

Nicole Greenhouse, RISE’s Operations and Program Manager, leads this process with an extraordinary level of care. She reviews applications closely, considers the story behind each response, and works through the many possible combinations to identify pairings with real potential.

There is both strategy and humanity in that work. A pairing may look logical on paper, but Nicole considers whether the two people are likely to communicate well, whether the mentor’s experience aligns with what the mentee actually needs, and whether the relationship can be valuable for both participants.

The work continues after introductions are made. RISE provides mentor training, guided discussion prompts, and structured session plans to help participants move beyond surface-level networking and into meaningful conversations. That support creates a framework while still leaving room for each relationship to develop naturally.

It is a high-touch process because the people entering the program deserve more than a name pulled from a spreadsheet.

Learning From Mentors Across the Industry

The impact of mentorship extends beyond those formally matched in the program. Through RISE Mentorship Monday, professionals at any career stage can hear directly from leaders and mentors across the insurance industry.

Upcoming conversations will cover topics including:

• Imposter syndrome
• Authenticity and professional presence
• Building your brand
• Executive presence and influence
• Career advancement

These are the kinds of career lessons people often learn through experience, but open conversations allow more professionals to benefit from them sooner.

Mentorship Monday sessions are open to everyone. You do not need to be enrolled in the formal mentorship program to attend, learn, and join the conversation. Visit the RISE events calendar to see upcoming sessions and register.

Building the Industry People Want to Stay In

There is no single solution to the insurance talent gap. But if the industry wants to attract people, retain them, and prepare them to lead, mentorship has to be part of the answer.

When people have access to guidance, honest conversations, and relationships outside the boundaries of their everyday roles, they can make more informed decisions about their careers. They are also more likely to recognize just how many opportunities this industry holds.

That is what the RISE Mentorship Program is built to do: connect people with the perspective, support, and relationships that help turn an insurance job into a lasting career.