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Darrow

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Updated Apr 25, 2026 · 21 sessions

Progress Assessment

Darrow is making meaningful enterprise progress — securing a ~$200K QBE design partnership, advancing Chubb and Zurich conversations, and building a 30+ lead pipeline with 6 high-intent opportunities — but has not yet converted these into recurring ARR. The company is pre-revenue or early-revenue in its insurance vertical, with long sales cycles (5+ year industry warning flagged by advisor) creating tension against board expectations. Momentum is real and accelerating into 2026, but no confirmed closed ARR figures are available to confirm on-track status.

Revenue (ARR)

No revenue figures found in session transcripts.

Open Threads 10

  • Send QBE design partnership first draft agreement to QBE and get contract signed by end of week (targeting May 11th London workshop)

    Since 2026-04 · mentioned 2×

  • Close Chubb scope and pricing call by end of quarter (April 29th call scheduled); target $400/report POC pricing

    Since 2026-04 · mentioned 2×

  • Negotiate QBE contract termination-for-convenience clause and payment-at-end terms using three-tier approach

    Since 2026-04

  • Send invoice approval to Kevin's team / forward unpaid invoices directly to Dan for processing

    Since 2026-04

  • Onboard at least 4 more design partners by end of Q1 (post-November MVP launch)

    Since 2025-10 · mentioned 2×

  • Respond to Beasley Claim team POC pricing inquiry (either provide $25K–$70K range or schedule call)

    Since 2025-11 · mentioned 2×

  • Leverage Moshe's insurance Rolodex to generate additional high-intent leads and facilitate strategic investor introductions

    Since 2026-02 · mentioned 2×

  • Identify and close 2–3 additional high-intent leads beyond current 8 to achieve 2026 revenue goals

    Since 2026-03 · mentioned 2×

  • Finalize Accessibility project scope and pricing for Wednesday session; confirm 30-day first milestone timeline

    Since 2026-03

  • Hire candidate with 15+ years insurance industry experience to help open pipeline doors

    Since 2025-10 · mentioned 2×

Stalled Initiatives 4

  • Beasley multi-year enterprise deal

    Beasley introduced in mid-2025 as world's largest insurance carrier with strong product enthusiasm; progressed through demo, scoping, and pricing negotiation stages but deal remains unsigned across 7+ sessions. Requires CEO-level back-channeling and faces law firm financial incentive misalignment issues.

    First raised 2025-07 · last mentioned 2026-02

  • Design partner onboarding beyond first MGA

    Goal of 4+ design partners by end of Q1 set in October 2025; only one confirmed design partner (MGA raising capital) mentioned across multiple sessions, with no additional signed design partners confirmed despite pipeline activity.

    First raised 2025-10 · last mentioned 2026-03

  • Evia engagement and conversion

    Evia appeared as a key early prospect from the first session and recurred through multiple sessions; relationship described as fragile with organizational stress and champion limitations; no closed deal confirmed after 8+ months of engagement.

    First raised 2025-07 · last mentioned 2026-02

  • Series C / fundraising round close

    Funding round described as ongoing from November 2025 through April 2026 with Georgian leading and $30M target from insurance players plus $10M from Georgian; round not yet confirmed closed across multiple sessions.

    First raised 2025-11 · last mentioned 2026-04

Playbook Gaps

Topics not yet covered in coaching sessions:

founder mindset leadership revenue operations customer success

Covered:

sales go to market fundraising hiring

Sales Call Patterns

No call reviews on file for this client.