Overview
You're building and leading a sales team (SDRs, AEs, or both) at an 87-person company that's scaling fast. You're hiring reps, coaching them on consultative health benefits sales, and building repeatable processes. You'll likely carry a small personal quota while managing 3-6 direct reports. This is player-coach mode, not pure management.
Role Snapshot
| Aspect | Details |
|---|---|
| Role Type | Player-coach sales manager |
| Sales Motion | Managing team across outbound and partnerships |
| Deal Complexity | Consultative to Enterprise (depending on team) |
| Sales Cycle | Varies by team (2-8 months) |
| Deal Size | N/A (managing team performance) |
| Quota (est.) | Team: $3-5M/year, Personal: $300-500K/year |
Company Context
Stage: Series A-B (estimated based on 87 employees and active hiring)
Size: 87 employees
Growth: Rapidly hiring across sales, demand gen, and go-to-market roles
Market Position: Challenger in health benefits space, scaling to compete with larger players
GTM Reality
Pipeline Sources:
- Outbound SDR motion (cold calls, broker outreach)
- AE self-sourcing (especially for enterprise deals)
- Broker partnerships (growing channel)
- Limited inbound (working with demand gen to build this)
Team Structure: You're building or managing a team of 3-6 reps (SDRs, AEs, or mixed)
Support Resources: Limited - no ops team, no dedicated enablement, minimal tools
Competitive Landscape
Main Competitors: Traditional PEOs, large benefit brokers, other ICHRA platforms
How They Differentiate: Direct primary care + ICHRA = cost savings + better access
Common Objections: Risk aversion, ICHRA education gap, broker resistance
Win Themes: Proven cost savings, mission-driven team, better employee outcomes
What You'll Actually Do
Time Breakdown
Coaching/1-on-1s (30%) | Hiring/recruiting (25%) | Deal support (20%) | Process building (15%) | Your own deals (10%)
Key Activities
- Hiring and onboarding: You're interviewing candidates, building job descriptions, and ramping new reps. Probably hiring 2-4 people in your first 6 months.
- Deal coaching: Jumping into complex deals to help reps navigate multi-stakeholder sales, handle objections on ICHRA, and close stalled opportunities.
- Process creation: Building sales playbooks, call scripts, objection handling guides, and qualification criteria. Most of this doesn't exist yet.
- Forecasting and pipeline reviews: Weekly pipeline reviews with each rep, rolling up forecasts for leadership, identifying at-risk deals.
- Personal deals: Carrying 1-3 of your own deals (usually larger or strategic accounts) to stay sharp and model best practices.
The Honest Reality
What's Hard
- You're building processes from scratch. There's no established playbook, no formal training program, no well-defined ICP yet.
- Coaching on health benefits sales is complex - reps need to understand ICHRA, ACA compliance, state regulations. You can't just teach "objection handling."
- Hiring is tough. You need reps who can handle consultative, education-heavy sales in a newer market. Most candidates want inbound leads and short cycles.
- You'll spend a lot of time in internal meetings aligning with product, implementation, and demand gen. The org is figuring things out.
- You're probably understaffed - you'll be doing manager work, individual contributor work, and ops work all at once.
What Success Looks Like
- Team hits $3-5M in annual bookings (depends on team size and mix)
- Reps ramp to full productivity within 4-6 months
- 80%+ of your hires work out (hit quota, stay past year one)
- You build repeatable processes that the next manager can use as the team doubles
Who Your Team Sells To
Primary Buyers:
- HR Directors/CHROs at 50-2,000 employee companies
- CFOs (especially for cost-focused conversations)
- Benefit brokers (partnership channel)
What They Care About:
- Reducing health benefits costs (20-40% savings)
- Avoiding employee complaints about healthcare access
- ACA and state compliance
- Simplifying benefits administration
Requirements
- 3-5+ years sales experience with 1-2+ years managing a team (or strong player-coach experience)
- Deep understanding of consultative, complex sales (benefits, insurance, HR tech, or similar)
- Experience building process and coaching reps in early-stage environments
- Comfortable with ambiguity - you'll be figuring out what works in real-time
- Hands-on mentality - you'll close deals, write content, and jump into the weeds
- Genuine care about healthcare access and improving outcomes (mission matters in this grind)