Product-Market Fit: How Tito Goldstein Found It After 2 Years of Near-Zero Revenue

Summary of Product-Market Fit: How Tito Goldstein Found It After 2 Years of Near-Zero Revenue

by Omer Khan

45m•January 29, 2026
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Overview of Product-Market Fit: How Tito Goldstein Found It After 2 Years of Near-Zero Revenue

Host Omer Khan interviews Tito Goldstein, co‑founder of TeamBridge, about the startup’s journey from a two‑year period of near‑zero revenue to multiple seven‑figure ARR and 200+ enterprise customers. The conversation covers how deep customer research exposed the real pain, why their first product missed the mark, the pivot to a composable workforce operating system, go‑to‑market lessons (especially around focus and storytelling), and practical sales tactics that improved close rates.

Guest background

  • Guest: Tito Goldstein — co‑founder of TeamBridge; ex‑product designer at Uber (led rider/driver experiences and internal tools).
  • Host: Omer (Omar) Khan — SaaS podcast.
  • TeamBridge mission: modernize workforce tools for hourly workers (the “forgotten demographic”) so employers can differentiate their employee experience and attract scarce talent.

What TeamBridge does

  • Product: a workforce operating system built from composable “Legos” (templates + configurable building blocks).
  • Use cases: find, attract, manage, engage and pay hourly workers; scheduling, automations, workflows, incentives, time tracking, learning, etc.
  • Value proposition: turn workforce software into a revenue/differentiation lever rather than a commodity admin tool — reduce admin time and surface opportunities to increase revenue.
  • Customers & scale: ~60 employees, multiple seven‑figure ARR, 200+ enterprise customers, 500k+ end employees, >$35M raised across seed/A/B.

The discovery → build → pivot story

  • Origin: Tito and cofounder Arjun’s experience interviewing thousands of Uber drivers revealed that drivers accepted lower pay for better agency via the app. That insight inspired building better worker-facing software for hourly industries.
  • Initial build: launched a scheduling product (seeded by product/design expertise and early prototypes).
  • Market feedback: customers said the core pain wasn't just scheduling — it was the “connective tissue” around scheduling: workflows, automations, and spreadsheet‑based processes.
  • Pivot: rebuilt the product around composability and automation. That rework took about a year — and the new product made more revenue in its first month than the old product had in two years.
  • Takeaway: use initial product releases to learn market truth; be willing to rebuild when you discover the real pain.

Go‑to‑market, ICP and storytelling lessons

  • Early approach: cast a wide net (movie theaters, restaurants, retail, stadiums, healthcare) to learn primitives across industries. Upside: broad learning; downside: lack of prioritization slowed product and GTM.
  • Focus shift: once product‑market fit signals came from specific verticals (notably medical staffing), they doubled down on adjacent markets with shared needs.
  • Messaging: early mistakes included trying to be everything to everyone. Improvement came from honest, focused storytelling — e.g., “we built at Uber, now we’ll bring that experience to your industry.”
  • Sales channels: began door‑to‑door, then during COVID moved rapidly to outbound (emails, calls, paid lead lists — Capterra, G2, Software Advice), Zoom demos, sponsorships and events.
  • Vertical playbooks: for every new vertical they explicitly do discovery to learn nuances (example: stadium staffing requires mass short‑notice staffing workflows; medical staffing has per‑diem vs travel nursing distinctions).

Sales approach & tactics

  • Question‑first selling: Tito recommends spending the first half of sales calls on discovery, not demos. Tailor demos to the one key value that surfaced in discovery.
  • Education required: buyers often expect plug‑and‑play tools; TeamBridge sells configurability — this requires education and early adopters willing to co‑create.
  • Outbound lessons: email/lead channels get saturated — but honest, well‑targeted messaging and consistent multi‑touch approaches build recognition and open doors.
  • Closing: once prospects see tailored demos that mirror their language and metrics, conversion improves substantially.

Biggest challenges & how they handled them

  • Sunk‑cost temptation: initial investment in the scheduling product could have trapped them; instead they listened and rebuilt.
  • Too broad ICP: spreading across many verticals delayed focus; remedy was to identify high‑signal verticals and go deeper.
  • Go‑to‑market skill gap: founders were product/design heavy; they hired GTM experts to sharpen focus and scale sales.
  • Investor pressure: low burn and multi‑year runway plus supportive investors gave them the space to iterate.

Notable quotes & insights

  • “Stand out or you become a commodity.” — on why composability matters for employers competing for hourly talent.
  • “The connective tissue — automations and workflows around scheduling — was the real pain.” — explains why the first product missed PMF.
  • “If you just start selling your product, and at the end they say ‘I didn’t want any of that,’ you’ve burned the opportunity.” — on disciplined discovery.
  • Tito’s advice: grit and curiosity are core founder attributes; be willing to let your former self die (change boldly when needed).

Lightning‑round highlights

  • Favorite pieces of advice: grit wins — the person who endures longest often succeeds.
  • Book recommendation: You Are Now Less Dumb (psychology, biases).
  • Productivity habit: fitness, sleep and general health as foundational for clarity and performance.
  • Fun facts: Tito is a maker (brew beer, make soap/paper), converting a Sprinter van into a camper, has a dog named Callie.
  • Contact: teambridge.com or Tito on LinkedIn.

Practical takeaways / Action items for founders

  • Do deep, repeated customer discovery across both end users and buyers — use early products as probes to uncover the real pain.
  • Start every sales call with structured discovery questions; only demo what directly maps to the prospect’s primary pain or metric.
  • Narrow ICP early enough to prioritize roadmap and GTM; then expand to adjacent verticals using composable primitives.
  • Tell an honest, focused story about where you are as a company — truth attracts the right early adopters.
  • Build composability when the market needs differentiation (allow customers to configure experiences that help them hire and retain talent).
  • Maintain low burn to buy time for learning and pivots if needed; align with investors who give runway for discovery.

Where to learn more