Director of Sales

Overview

You'll manage a team of Enterprise AEs selling Collectly's AI-powered RCM platform to healthcare providers—private practices, medical groups, billing companies, and health systems. You're coaching reps through complex, multi-stakeholder deals in healthcare where buying committees are large, switching costs are high, and procurement moves slowly. You report to the VP of Sales and are responsible for team quota attainment, forecast accuracy, and building out processes that didn't exist before.

Role Snapshot

Company Context

Stage: Growth stage (93 employees, actively scaling)

Size: 93 employees

Growth: Hiring Enterprise AEs, building out the sales org, VP of Sales actively recruiting leadership

Market Position: Challenger in healthcare RCM competing against established vendors. Selling "AI-native" as differentiator in a space where buyers are conservative about technology changes.

GTM Reality

Pipeline Sources:

• 30-40% Inbound - Some marketing-generated leads, but healthcare buyers typically don't convert quickly from content
• 60-70% Outbound - Cold outreach to practice administrators, CFOs, revenue cycle directors. Lots of LinkedIn, targeted calling into specific specialties
• Small amount from referrals/existing customer expansion

SDR/AE Structure: Likely building out SDR support, but AEs still do significant self-sourcing

SE Support: Shared SE resources for technical demos and EHR integration discussions

Competitive Landscape

Main Competitors: Likely competing against legacy RCM vendors (Waystar, R1 RCM, Change Healthcare), other AI-powered billing tools, and internal/status quo (practices using their existing EHR's billing module)

How They Differentiate: AI-native platform that automates patient engagement and collections workflows, EHR-agnostic integration

Common Objections: "We already have billing software," concerns about AI accuracy with sensitive patient data, integration complexity with existing EHR systems, change management risk for staff

Win Themes: Better cash flow and collection rates, reduced manual work for billing staff, improved patient payment experience

What You'll Actually Do

Time Breakdown

Coaching/1:1s (30%) | Deal Reviews (25%) | Forecasting/Planning (20%) | Hiring/Recruiting (15%) | Internal Meetings (10%)

Key Activities

• Weekly pipeline reviews with each AE: You're digging into their top 10 deals, asking hard questions about champion strength, economic buyer access, competitive threats. Most deals will be stuck in "technical evaluation" or "waiting on committee decision" for weeks.
• Deal coaching and strategy: Jump into calls with AEs when they're stuck, help navigate multi-stakeholder dynamics (practice manager likes you, but CFO is skeptical about ROI). You're pattern-matching from your own enterprise sales experience.
• Forecasting and pipeline management: Every week you're scrubbing pipeline with the VP, explaining why deals are slipping quarters, defending your commit number. Healthcare deals slip constantly—procurement delays, budget freezes, competing priorities.
• Hiring and ramping new AEs: Interviewing candidates, onboarding new reps, getting them up to speed on healthcare RCM domain knowledge they probably don't have. There's no formal playbook yet—you're building it.
• Cross-functional alignment: Meetings with Product on what features customers need for POCs, with Marketing on lead quality, with Customer Success on handoffs. At 93 people, you're still building these processes.

The Honest Reality

What's Hard

• Healthcare sales cycles are brutal—6-9 months is optimistic. Deals get delayed for budget cycles, regulatory concerns, implementation capacity. Your reps will get frustrated.
• You're managing both up and down—coaching AEs who might be struggling while also managing the VP's expectations on pipeline and explaining why healthcare doesn't move as fast as SaaS.
• At this stage (93 people), there's limited infrastructure. You're building forecasting models, comp plans, territory assignments, and playbooks while also hitting quota. It's player-coach reality.
• Healthcare buyers are risk-averse. They need extensive proof, reference calls, security reviews, BAAs. Deals stall in procurement for months after verbal commitment.
• Your reps will complain about lead quality, product gaps, long implementation times. You're the buffer between them and executive pressure.

What Success Looks Like

• Team hits 85-90%+ of quota consistently, with predictable pipeline coverage (4-5x in healthcare)
• Forecast accuracy within 15-20% each quarter—you actually know which deals will close
• Reduced ramp time for new AEs from 6 months to 4 months because you've built better onboarding
• Clean pipeline hygiene—deals are qualified properly, not sitting in stage 3 for 4 months with no activity

Who You're Selling To

Primary Buyers:

• Revenue Cycle Directors / VP of Revenue Cycle (day-to-day owner)
• CFOs / Practice Administrators (economic buyer, final approval)
• IT/Integration teams (technical veto power on EHR compatibility)
• Sometimes CMO/COO at health systems level

What They Care About:

• Days in A/R and collection rates—will this actually improve cash flow?
• Staff burden reduction—billing teams are overworked and understaffed
• Patient satisfaction scores—fewer billing complaints
• Implementation risk—can't disrupt current revenue flow during transition
• Security and compliance—HIPAA, data privacy, BAA requirements

Requirements

• 5+ years of enterprise B2B sales experience with at least 2-3 years managing quota-carrying AEs
• Experience selling complex SaaS deals with 6+ month cycles and multiple stakeholders
• Healthcare/RCM experience is a major plus but not required—you need to learn the space quickly
• Track record of building processes and playbooks in growth-stage companies (not looking for F500 managers who expect infrastructure)
• Comfortable with ambiguity—this isn't a well-oiled machine, you're building it
• Experience hiring, ramping, and coaching AEs to quota attainment
• Strong forecasting discipline and pipeline management skills
• Willingness to roll up sleeves and jump into deals when needed (player-coach, not hands-off)