Build Sales Strategy for SMB SaaS

Company Context

FlowSync is a B2B SaaS company that sells workflow automation software to small and mid-sized businesses. The company has reached $8M ARR, operates in the US and Canada, and serves 1,200 customers across professional services, healthcare administration, and light manufacturing. Historically, growth has come through founder-led sales and inbound demand, but growth has slowed from 55% YoY to 24% YoY over the last 12 months. The CEO wants a more deliberate sales strategy to accelerate growth and improve sales efficiency.

Strategic Situation

FlowSync must decide how to structure its sales strategy for the next 12 months. The company currently sells a single product with annual contracts ranging from $6K to $30K ACV, but win rates vary widely by segment and the team lacks a clear view on where to focus. Management is debating whether to prioritize SMB self-serve/light-touch sales, mid-market outbound sales, or a vertical-focused approach built around healthcare administration, where recent customer retention has been strongest. The decision matters now because the company plans to hire up to 6 additional quota-carrying reps next year and has only one planning cycle to get the model right.

Data Points

Additional facts:

• Current pipeline mix: 55% SMB, 35% mid-market, 10% healthcare niche
• Marketing budget next year: $1.8M, up from $1.2M
• Board target: reach $12M ARR within 12 months while keeping CAC payback under 18 months
• Product team can support only one major packaging/pricing change and two segment-specific features in the next year

Deliverables

You are the incoming Head of Revenue Strategy. Prepare a recommendation for the CEO and board:

1. Assess which customer segment(s) FlowSync should prioritize in its sales strategy over the next 12 months.
2. Size the near-term revenue opportunity and estimate what mix of new bookings is required to reach the ARR target.
3. Evaluate the trade-offs across segment attractiveness, competitive intensity, and sales efficiency.
4. Recommend a go-to-market model, including channel mix, sales coverage, and resource allocation.
5. Outline a 12-month execution plan with success metrics and major risks.

Constraints

• Hiring capacity is limited to 6 new reps and 2 customer success hires this year.
• The company cannot pursue all segments equally; leadership wants a clear prioritization.
• Cash is available, but the board will not support a strategy that pushes CAC payback above 18 months.
• Product and marketing resources are limited, so positioning must remain relatively focused.