From Data to Direction: Smarter Strategies for Small Business Leaders

Every Day Is Reactive. This Session Is Designed to Change That.

Running a small business means making high-stakes decisions about benefits, people, and compliance without the dedicated teams, budgets, or infrastructure larger organizations take for granted. Most small business leaders are not lacking ambition. They are lacking the time and support to get ahead of the decisions that keep compounding.

Only 6% of small businesses have a multi-year benefits strategy. The ones that do spend less and retain more. That gap is not about resources. It is about having the right framework and the right guidance at the right moment.

This webinar brings together a team of Gallagher small business specialists to give you both.

What You Will Learn:

• How to evaluate your current benefits approach against a multi-year strategy framework and identify the gaps that are costing you money and talent right now
• What employees at small businesses want most, and why your organization has a cultural advantage over larger employers that most owners are not leveraging intentionally
• Which compliance requirements apply to your business today, including the thresholds that trigger a cascade of federal obligations many owners do not discover until they are already behind
• How to think about alternative funding strategies and plan design options that work at your size without blowing your benefits budget
• What a proactive HR and people strategy looks like for a lean organization, and how to build one without adding headcount
• How to walk into your next conversation with a broker, consultant, or leadership team armed with specific, data-backed language that moves the discussion forward

Why This Matters Now

The fear of an audit, a compliance gap, or a resignation that could have been prevented is not abstract for small business leaders. It is the background noise of every week. And when every day is spent in reactive mode, strategic planning starts to feel like a luxury rather than a necessity.

It is not. The small businesses pulling ahead are not the ones with bigger budgets. They are the ones that made a few deliberate shifts earlier than everyone else. This session gives you the data and the direction to make those shifts.

Your Presenters

• Dean Klune, Divisional Vice President, Small Business Solutions, Gallagher
  Dean hosts today’s session and brings deep expertise in small business benefits strategy, helping organizations move from renewal-to-renewal survival mode into a more intentional, multi-year approach.
• Jackie Neum, Small Business Consultant, Gallagher
  Jackie specializes in benefits planning and cost management for small employers, helping organizations build programs that work within real budget constraints.
• Matt Van Dyke, Benefits Advisor, Gallagher
  Matt focuses on alternative funding strategies and plan design for small employers looking for smarter, more sustainable benefits structures.
• Kathleen Schultz, HR and People Consultant, Gallagher
  Kathleen brings expertise in employee engagement and retention for small organizations, helping leaders understand what is driving turnover and what to do about it.
• Brian Tolbert, Small Business Advisor, Gallagher
  Brian specializes in culture, voluntary benefits, and workforce strategy, helping small business owners build environments where people want to stay.
• Lindsay Paris, Compliance Specialist, Gallagher
  Lindsay focuses on regulatory requirements for small and mid-sized businesses, helping organizations understand what applies to them and where their exposure lives.
• Stephanie Murphy, HR Compliance Consultant, Gallagher
  Stephanie helps small business owners navigate complex and evolving compliance requirements, making sure they are not caught off guard by changes they did not know were coming.

Who Should Attend

• Small business owners, CEOs, and COOs making benefits and people decisions without a dedicated HR department
• HR leaders at organizations with 10 to 250 employees who are wearing multiple hats and managing compliance alongside everything else
• Business leaders who are cost-conscious and growth-minded but worried that turnover or compliance gaps could derail their momentum
• Anyone who feels like they are in survival mode at every benefits renewal and is ready for a more strategic approach
• Leaders who are working with a broker or consultant but feel like they are not getting enough proactive guidance

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