Director of Sales

Overview

You're leading a team of Enterprise AEs selling Collectly's AI-powered revenue cycle management platform into healthcare providers—private practices, medical groups, health systems, and billing companies. You'll be player-coaching: closing your own deals with larger accounts while building pipeline discipline, deal methodology, and coaching cadence for your team. Healthcare sales means navigating multiple stakeholders (practice administrators, CFOs, IT), long evaluation cycles, and integration concerns with existing EHR systems.

Role Snapshot

Company Context

Stage: Series A/B stage (estimated based on 93 employees and growth trajectory)

Size: 93 employees

Growth: Actively hiring, VP of Sales posting directly suggests expansion mode

Market Position: Challenger in the healthcare RCM space—competing against established players with an AI-first approach. The "AI-native" positioning suggests they're trying to differentiate in a crowded market where most incumbents are adding AI features to legacy systems.

GTM Reality

Pipeline Sources:

• 30-40% Inbound - Healthcare providers searching for RCM solutions, likely some demo requests from website and limited content marketing
• 50-60% Outbound - Cold calling into practices, health systems, and billing companies. Your AEs are doing a lot of list building and multi-threading into accounts
• 10-20% Referrals/Partners - Some word-of-mouth in healthcare circles, possible integration partnerships with EHR vendors

SDR/AE Structure: Likely small or no dedicated SDR team at 93 people—AEs are probably doing significant self-sourcing

SE Support: Probably shared SE support given company size; demos require showing integrations and technical capabilities

Competitive Landscape

Main Competitors: Established RCM platforms (like Waystar, Change Healthcare, R1 RCM), traditional billing companies, and other AI-powered newcomers

How They Differentiate: AI-native platform vs bolt-on AI features; EHR-agnostic integration; automation across the full patient financial experience

Common Objections:

• "We already have an RCM system"
• "How does this integrate with our [specific EHR]?"
• "We need to see ROI proof from similar-sized practices"
• "Our IT team needs 6 months to evaluate any new system"

Win Themes: Measurable improvement in collections rates, reduced days in A/R, lower cost per collection than current process

What You'll Actually Do

Time Breakdown

Own Deals (30%) | Team Coaching (25%) | Pipeline Reviews (20%) | Recruiting/Hiring (15%) | Internal (10%)

Key Activities

• Running your own enterprise deals: You're working 4-6 active opportunities with health systems or large medical groups. This means multi-stakeholder orchestration—practice administrators who feel the pain, CFOs who control budget, IT who gatekeep implementation. You're doing discovery calls, ROI analyses, demos with the SE, navigating procurement processes.
• Deal reviews with AEs: Weekly 1:1s where you're going deal-by-deal through their pipeline. You're coaching on qualification (is this real?), multi-threading strategy (who else needs to be involved?), and objection handling. You're listening to call recordings and giving specific feedback on discovery questions and value articulation.
• Building sales process: At 93 people, process is still being figured out. You're defining what "qualified" means, building out the pipeline stages in the CRM, creating talk tracks for common objections, and establishing forecast hygiene. This isn't handed to you—you're creating it.
• Recruiting and ramping AEs: You're probably hiring 2-3 more AEs this year. That means screening candidates, selling them on joining, and then spending significant time in the first 90 days getting them productive. Healthcare sales has a learning curve—your new hires need to understand RCM, get comfortable with clinical terminology, and learn the integration landscape.

The Honest Reality

What's Hard

• Healthcare sales cycles are long and unpredictable. Deals that look like they'll close this quarter slip because an IT committee needs to review security, or because the practice is in the middle of an EHR migration, or because budget just got frozen. You'll spend a lot of time chasing and re-engaging.
• At 93 people, you don't have full support infrastructure. Marketing is limited, there's no deep enablement team, comp plans might need adjusting mid-year. You're building while flying.
• Your team is selling against the status quo as much as against competitors. Healthcare providers are risk-averse and change-resistant. Most of your losses won't be to a competitor—they'll be to "we're going to stick with what we have."
• The "buffalo" metaphor in the job post is telling you this is a high-intensity environment. The VP is explicitly looking for someone who runs toward chaos, which means you should expect chaos.

What Success Looks Like

• Your team consistently delivers 85-90% of quota quarter over quarter
• Pipeline coverage is 4-5x quota with real, qualified opportunities (not wishful thinking)
• You've built repeatable plays for different customer segments (small practices vs health systems)
• AEs can articulate ROI in healthcare terms and navigate multi-stakeholder deals without you in every call
• You close 2-3 of your own strategic deals per year that become case studies

Who You're Selling To

Primary Buyers:

• Practice Administrators / Office Managers (mid-market practices)
• CFOs / Revenue Cycle Directors (health systems, large groups)
• Billing Company Executives (if selling to RCM outsourcers)
• IT/Compliance (technical evaluation and security review)

What They Care About:

• Hard ROI: improvement in collection rates, reduction in days in A/R, cost per collection
• EHR integration: will this actually work with our Athenahealth/Epic/eClinicalWorks/etc.?
• Patient experience: they don't want to hurt patient satisfaction scores with aggressive billing
• Implementation risk: how long until we're live, how much staff time is required, what if it breaks our existing workflow?
• Compliance: HIPAA, data security, audit trails

Requirements

• 5+ years leading enterprise sales teams, ideally in healthcare SaaS or fintech
• Track record of carrying personal quota while managing a team
• Experience building sales process and methodology in a fast-growing company (Series A/B stage preferred)
• Familiarity with healthcare buying cycles—understanding of how health systems and medical practices evaluate and purchase software
• Comfortable with ambiguity and building as you go; this isn't a Fortune 500 playbook execution role
• Located where you can collaborate with the team (remote policy unclear, but expect some travel for QBRs and team meetings)