When to sunset products and handle enterprise security assessments

Executive overview

Successful founders often face the challenge of managing multiple products at different growth stages. This episode addresses six critical questions from SaaS founders: whether to discontinue a slower-growing product, how to handle enterprise security assessments, managing lifetime deals in acquisitions, using customer credibility in sales, and protecting IP when building side projects at your employer.

Focus ruthlessly on your growth leaders, not past successes.

When to sunset a slower product

Kill a product if a newer offering is growing 3x faster and generating 3x more revenue. Sunk cost fallacy keeps founders attached to early products. Instead of maintaining separate plans and complexity, consolidate: raise prices on the legacy product, simplify its offerings to a single tier, or discontinue it entirely to direct all energy toward your growth engine.

Enterprise pricing requires separate tier strategy

Don't fork your product into separate brands or companies to serve different price tiers. Instead, layer your pricing: maintain low-touch, self-serve plans under $50/month, and create a distinct high-touch enterprise plan with custom pricing (often 10-20x higher). This dual-funnel approach captures both markets without splitting your focus. Raise the price; don't splinter the company.

Handling undisclosed lifetime deals in acquisitions

The seller has a legal obligation to disclose lifetime customers during due diligence. If not disclosed, this may breach contract or constitute fraud depending on your agreement and jurisdiction. Before escalating legally, assess the actual damage: query your database for active users among the lifetime customers (many churn over time). If only 20-30 remain active, the cost may not justify legal pursuit. Focus your effort on acquiring 10-20 new customers per month instead; organic growth will make the issue inconsequential.

Security assessments as a gating mechanism

Enterprise buyers always demand SOC 2 certification or security questionnaires (often 150+ questions). Don't answer these questions for individual licenses or small deals—require a minimum annual contract value of $20K-$40K. Once you hit that threshold, invest in SOC 2 certification as your silver bullet: it eliminates the need to answer custom questionnaires from most enterprises.

Leverage customer credibility in sales and marketing

Co-founder status combined with customer experience is a powerful differentiator. Lead with it: "I ran a sports business for 10 years—I know exactly what you need." Use real customer examples to show how the product solves your own problems. Be transparent about not being a sales person; emphasize that you weigh in on product direction and understand the industry deeply. This disarms enterprise buyers and builds instant trust.

Side project IP—get explicit written permission

Before building a side project related to a problem at your current employer, get written approval from your company (typically via an HR form or explicit signed agreement). Employment contracts vary by state and country; some claim ownership of anything you build, others don't. Gray areas on IP are dangerous. Two examples of founders who got explicit permission before building avoid any dispute. Always check your employment agreement first, then disclose to HR or your CEO.