A Briefing: The Operators Playbook for 2027

The new year is coming fast, and the operators who win in 2027 are the ones planning for it now. This event is built to get you the whole picture in one sitting.

Rather than a single panel going deep on one topic, The Operators 2027 Playbook brings several experts to the front of the room — to brief you on critical domains, including: marketing, sales, AI, human resources, funding, and the economic outlook. These rapid-fire reports will cover the shifts that matter most heading into next year.

Every briefing brings clarity to what's changing in 2027, the specific moves to make and the traps to avoid. No fluff, no filler, just clear delivery of the signals you need to plan your year.

You'll leave with a cross-functional read on what's ahead: where to point your marketing dollars, what AI actually changes for your business, how the labor and benefits landscape is shifting, what the funding environment looks like, and how the economy frames all of it. Then the floor opens so bring your questions for the experts, and stay to connect with the operators and advisors who make up the Club E room.

If you run something, this is the fastest way to walk into 2027 with a plan.

Jennifer Libby - District Manager SPHR GPHR, Insperity

Jennifer Libby has spent more than three decades in the rooms where people decisions get made. She led HR inside manufacturers running union workforces and round-the-clock operations at Phillips Plastics, Cybex International, and Daikin Applied, served as a director-level HR business partner at UnitedHealth Group, and spent three years as President and CEO of the Owatonna Area Chamber of Commerce, representing more than 575 businesses and roughly 14,000 employees across the region. Today she is a District Manager at Insperity, where she helps Twin Cities small and midsize companies carry the full weight of the employer role: recruiting and retention, benefits and healthcare costs, payroll and compliance, and the workforce planning that determines what next year costs. That combination, decades inside the HR chair plus a current view across the many companies she advises, is exactly what a rapid-fire briefing demands. In December, Jennifer takes the HR desk: the shift reshaping how owners will hire, retain, and pay people in 2027, the specific moves to make before January, and the trap that will cost operators the most.

Darin Lynch - Founder & CEO, Irish Titan

Darin Lynch is the founder and CEO of Irish Titan, the Minneapolis digital commerce agency he built to help businesses create ecommerce that strengthens the whole company, not just a standalone website. Working from a "Business First. Online Second" philosophy, the idea that an online store should serve the entire business rather than sit off to the side, Irish Titan designs, builds, and grows ecommerce channels, and its reputation has made it a longtime fixture of the Twin Cities entrepreneurial community. Darin's read on marketing is anchored in results rather than impressions: he launched three national retailers' first ecommerce channels before founding Irish Titan in 2004, and for two decades since, his team has been judged on whether the marketing actually moved revenue, across search, paid media, email, and the site itself. That track record gives him an unusually honest scorecard on what works, what wastes budget, and what customers respond to. In December, Darin takes the marketing desk: the shift reshaping how customers find and buy in 2027, where to point your marketing dollars before January, and the trap that will burn the most budget.

Andrew Dahlen - President, Highland Bank

Andrew Dahlen is the President of Highland Bank, the family-owned Twin Cities community bank and SBA Preferred Lender that has been financing small and mid-sized businesses since 1943. He has spent nearly four decades in banking and has held almost every seat in the building: he started as a teller in 1988, worked up through personal banking, branch management, and sales leadership at U.S. Bank, then joined Highland in 2003, where he led commercial banking, branch banking, and sales before being named President in July 2025. That path means he has sat on both sides of the lending conversation, beside the owner asking for capital and inside the credit decision, through every rate environment and credit cycle since the late 1980s. Few people in the room will have a clearer read on what banks will and won't fund heading into the new year. In December, Andrew takes the funding desk: the shift in how banks will lend to operators in 2027, the moves to make before you need the money, and the trap that gets good loan requests declined.

Insperity

Irish Titan

Breakthrough Impact Group

Highland Bank

Lab 651

Recursive Awesome