De-Risking Outbound: Launch Strategy for a Health Tech Pilot

A health benefits platform, had established product-market fit and was preparing to scale its outbound sales efforts. With a defined ICP—targeting account managers at insurance agencies—and a growing cold lead database, the COO sought guidance on whether cold calling could become a viable demand generation channel before committing internal headcount or engaging outside vendors.

However, the company lacked:

• In-house SDR infrastructure
• A tested outreach sequence
• A defined process for hiring and managing SDRs

Key challenges included:

• No Existing Sales Development Function: Health Benefits Technology had no internal SDRs or playbook in place to test or scale outbound prospecting.
• Unstructured Outreach Process: While cold and warm leads were available, there was no defined outreach cadence or messaging hierarchy tailored to buyer personas.
• Lack of Hiring Framework: The team needed a clear process for sourcing, vetting, and managing SDR talent, whether internal or outsourced.
• Unvalidated Cold Calling Channel: Health Benefits Technology’s leadership wanted to test cold calling without over-investing—but had no benchmarks, strategy, or infrastructure to do so safely.

I developed a tailored outbound Sales Playbook and Pilot Strategy to help Health Benefits Technology test cold calling in a low-risk, data-informed manner. This included:

Outbound Strategy Definition: 

• Outlined a 30–45 day cold calling pilot to assess viability and performance benchmarks (connect rate, dials-to-demos ratio, objection themes, etc.).
• Positioned the pilot as a signal-gathering initiative to inform future scale-up decisions.

Sales Playbook Design

• Defined KPIs: Connect rate, dials-to-demos ratio, and demo volume targets (2–3 per week).
• Sequence & Messaging: Developed a multi-touch outbound cadence—Clay-sourced list → LinkedIn → cold call → email follow-up—tailored to the pain points of overworked account managers in regional insurance offices.
• Created messaging frameworks focused on COBRA bases challenges for Account Managers.
• Identified four critical buyer intent signals (e.g., M&A, branch expansion, new leadership).
• Recommended dialer tools and CRM integrations (e.g., Clay, Slack-integrated site visitor intelligence).

Pilot Strategy Setup

• Framed cold calling as a dual-purpose channel: both discovery and conversion.
• Proposed a 30–45 day test window to validate channel effectiveness.
• Provided volume benchmarks (200–300 dials/week) and outlined a rep coaching cadence.

SDR Hiring and Oversight Path: 

• Recommended a fixed-fee SDR hiring model and shared vetted external sourcing options.
• Defined onboarding timelines, ramp-up schedules, and management structure (weekly 1-on-1s and daily huddles).

Enablement Materials & Execution Support

• Defined key SDR onboarding assets, objection-handling themes, and message calibration guidance.
• Delivered recommendations for tool setup, KPI reporting, and feedback loops to inform future channel investments and GTM sequencing.

By the end of the advisory phase, Health Benefits Technology had a fully structured outbound pilot plan, aligned tooling recommendations, and a clear decision path for SDR recruitment or agency support. I also connected them with vetted SDR hiring resources.

Immediate Results:

• Defined a measurable cold calling test strategy without overcommitting resources
• Gained executive alignment on KPIs, buyer personas, and messaging
• Received actionable guidance on SDR recruitment, onboarding, and performance coaching
• Integrated feedback loops and volume benchmarks to track performance and refine messaging during the pilot
• Recommended a lightweight tech stack to support pilot execution, including Clay, dialer tools, and visitor tracking

Strategic Impact: 

• Equipped the COO with a decision-ready outbound model, helping Health Benefits Technology move from “unsure” to “pilot-ready” in under 10 days
• Positioned the company to test outbound in-market with high clarity, improving odds of validation
• Reframed cold calling as a discovery and conversion tool—building executive confidence in testing and learning
• Reduced risk of wasted spend on SDR agencies before internal systems and messaging were dialed in
• Enabled the org to independently launch, run, and learn from the pilot—accelerating GTM readiness without outside dependency