Hard Decisions, Clear Thinking: Lessons from a Founder, CEO, and Investor

In this interview / fireside chat conversation with Jeff Epstein, we'll hear about his experiences as a founder, a CEO, and an angel investor. 

Jeff Epstein is the founder of Onboard.io, former CEO of Ambassador Software, and an angel investor in over 100 startups. He is a lawyer and a lifelong entrepreneur. 

Over the years Jeff has seen a lot and is happy to help other founders, especially in the following areas: 

1. Team-building
2. Culture
3. Enterprise sales
4. Customer onboarding
5. Fundraising
6. Board management and legal.

Summary

This Expert Session with Jeff Epstein dug into the lived realities of building and scaling B2B SaaS companies. Jeff — attorney-turned-serial-entrepreneur (Ambassador, Onboard) and angel investor — shared practical, candid advice on decision-making, hiring and firing, culture, sales incentives, onboarding, and founder priorities.

Why hard decisions get easier

• Decision-making is a muscle: the best leaders make decisions quickly, having already visualized many scenarios.
• Avoid bottlenecks: rapid decisions reduce friction and build trust; letting issues fester creates bigger problems.
• Prioritize fires: most problems are not existential — learn to tell which ones truly need immediate attention.

Hiring, culture, and people management

• Hire for attitude first: skill can be taught, culture fit usually can’t. “Brilliant assholes” cost more than they deliver.
• Set expectations early and explicitly: telling candidates “this is not an easy job” and documenting responsibilities prevents future disappointment.
• Promote from within when possible: internal promotion preserves culture and signals commitment, but be honest if someone doesn’t scale into a new role.
• Make tough calls fast: delayed firings often worsen outcomes for the team and company; clear feedback and written improvement plans help surface real change quickly.

Evolving the team as you scale

• Career-path conversations matter: not everyone wants the same trajectory (IC vs. manager/executive). Ask and plan.
• Hire over people when necessary, but give loyal, culture-aligned teammates a chance to grow into bigger roles.
• Be realistic about timing: longer, steadier growth (vs. hypergrowth) changes how and when you reorganize.

Sales compensation and alignment

• Commission-only or commission-heavy models work: salespeople need money incentives to thrive; salary-only sales teams typically underperform.
• Align incentives to business health: pay commissions when the business gets paid; reward renewals and multi-year deals to reduce churn and encourage quality customers.
• Avoid perverse incentives: structure commission plans to favor long-term, healthy customers rather than short-term revenue.

Onboarding and retention

• Onboarding is a retention lever: poor onboarding is a leading cause of churn.
• Start onboarding immediately after purchase: set expectations, surface required actions, and maintain momentum.
• Productize and document the onboarding path so customers know what to expect and how to succeed.

Founder questions most missed

• Ask who/what you’re optimizing for: company growth, personal life, family — these priorities don’t always align and require deliberate choices.
• Over-communicate: clarity about expectations (for teams, customers, and personal commitments) prevents misunderstandings and builds trust.
• Plan for intensity bursts: sustained high-intensity work is hard to maintain — be honest about trade-offs and timelines with teams.

Memorable advice and tone

• Be decisive, set clear expectations, and communicate relentlessly. Jeff repeatedly stressed proportionality: most issues aren’t catastrophes, and many harms are mitigated simply by speaking clearly and early.
• Culture and values are the company’s North Star. Living those values (not just posting them) attracts the right people and sustains performance.

Practical takeaways

• Write down role expectations and follow up within 1–2 weeks when performance is in question.
• Build commission plans that reward payment timing and renewals, not just signed contracts.
• Automate and begin onboarding the minute a contract is signed — preserve momentum and reduce churn.
• Hold regular career-path conversations and be honest when an employee’s ambitions don’t match the company’s needs.

This session blended tactical how-tos with founder psychology — emphasizing that practical systems (clear expectations, aligned incentives, documented onboarding) plus the discipline to act quickly are the building blocks of lasting SaaS success.