How Rising Team shifted from bottom-up to enterprise go-to-market

Executive overview

Selling to individual managers takes nearly as much effort as closing an enterprise deal — but the revenue is a fraction of the size. Jen Dalsky, founder of Rising Team, discovered this early and pivoted entirely to top-down selling, winning customers like Adobe, Google, Hershey's, and Airbnb.

The episode covers three compounding lessons: why top-down beats bottom-up, how pricing must match the way buyers think, and a simple one-to-ten qualifying rule that makes founder-led sales efficient.

The core insight: enterprise selling is pain-discovery, not persuasion — qualify fast, spend time only on high-probability deals.

Bottom-up vs. top-down

• Selling to an individual manager required nearly the same effort as closing an enterprise org of hundreds.
• Once that unit-economics reality was clear, Rising Team cut all bottom-up investment.
• Top-down entry points are typically a single org or business unit, not the whole company.
• Strong product retention creates internal propagation — users who move teams bring the product with them.

The 30-minute one-to-ten rule

• In every first meeting, rate the opportunity 1–10 before the call ends.
• A 10: they desperately need the product — invest heavily.
• A 2–3: determine that quickly, then nurture passively via email only.
• The goal is not to sell; it is to uncover pain and assess fit without wasting further cycles.
• If the product genuinely solves their problem, the close follows naturally.

Pricing and packaging evolution

• Seat-based pricing (per user/month) was logical but didn't match how buyers budget in the HR/leadership space.
• Shifting to per-manager pricing aligned with how companies think about spend on leadership development.
• Benchmark comparison: an executive coach costs tens of thousands; Rising Team replaces that at a fraction of the price.
• Transition tactic: show both pricing models side by side, let customers choose, then use that signal to commit to the new model.
• Usage-based AI pricing now sits on top of the subscription as the product becomes more AI-heavy.
• Watch for the winner's curse — if buyers agree too quickly, you're leaving money on the table.

ICP and lead channel discipline

• Early ICP: companies of 5,000+ employees, hybrid or distributed teams, low Glassdoor scores.
• Many early lead channels brought in non-ICP companies; 2025 was spent narrowing to channels that deliver ICP leads only.
• High-touch channels (executive dinners, targeted events) have been the most ROI-positive — one or two conversions per event justify the spend.
• Founder-led sales worked until pipeline exceeded capacity; enterprise sellers were hired only once viable lead channels were proven.

Adapting product to a shifting market

• The 2021 "remote team connection" use case lost urgency as companies returned to office and employer leverage shifted.
• Rising Team responded by pivoting the roadmap entirely in October — all new tracks built against an AI-first product vision branded Super Manager AI.
• Four pressures companies face now: efficiency demands, constant transformation (M&A, leadership changes), hybrid work, and AI adoption pressure.
• The winning package: AI amplification of managers plus periodic synchronous team sessions to preserve human connection.
• AI role-play (modelled on Jen's Stanford class) lets managers practice difficult conversations privately before having them for real.

Land and expand mechanics

• Enter via a single org; prove measurable impact (talent retention metrics are the most persuasive).
• Employees who change internal roles bring the product into new orgs organically — no additional sales motion required.
• Two levers for expansion: more products to the same buyers, or the same products to more buyers inside the account.
• Create mild internal FOMO — if one team has it and another doesn't, that imbalance drives inbound requests.