Director of Enterprise Sales

About Collectly

Collectly is a fast-growing healthcare technology company transforming revenue cycle management (RCM) through AI-driven automation. Millions of patients navigate inefficient billing systems every day, while providers face delayed payments, rising administrative burden, and operational complexity.

Collectly applies artificial intelligence to automate workflows, accelerate cash flow, and modernize the patient financial experience; enabling healthcare organizations to operate more efficiently and focus on delivering care.

There could not be a hotter space to play in.  Healthcare is a $4.9T industry and is adopting AI technology at 2.2x the rate of the rest of the economy.  RCM is at the heart of this transformation as it has a clear and demonstrable ROI to our customers.  

The Opportunity

We are hiring a Director of Enterprise Sales to lead and elevate our enterprise revenue motion during a critical phase of growth.

This leader will manage a team of experienced Enterprise Account Executives and be responsible for driving predictable revenue performance through stronger pipeline discipline, sharper enterprise deal strategy, and rigorous execution.

This is a hands-on leadership role for an operator who can step into complex deals, elevate diagnostic depth, strengthen outbound accountability, and build the operating cadence required to win consistently.

We are not seeking a passive forecast manager. We are looking for a leader who improves how enterprise sales is executed.

Please note: This role is hybrid - candidates located in the San Francisco Bay Area only will be considered.

Key Responsibilities

• Lead Enterprise Revenue Performance: Manage and coach 6 Enterprise Account Executives selling into healthcare organizations. Improve discovery depth, workflow diagnosis, and economic value articulation. Standardize deal strategy reviews and win-plan development. Increase qualified-to-close conversion rates and reduce performance variance.

• Strengthen Pipeline Health and Discipline: Establish clear expectations for pipeline coverage and opportunity creation. Reinforce AE ownership of prospecting and outbound consistency. Inspect leading indicators across pipeline stages to identify gaps early. Partner with Sales Development and Marketing to improve meeting quality and early-stage conversion. Lean into key partnerships to help drive top of funnel and increase win rates.

• Elevate Strategic Execution: Join strategic calls and materially improve outcomes. Diagnose stalled opportunities and define actionable paths to close or disqualify. Help your team connect pain to value and quantify impact to strengthen the business case in key deals. Coach reps in real time and in Gong on executive engagement, urgency creation, and multi-threading. Run plays to compete and win when there is an identified project, and slow down and educate when we’re creating the project. Identify opportunities to improve the overall motion and partner with the VP of Sales and Executive team to drive change across the GTM organization.

• Build Operations Cadence: Implement disciplined weekly inspection rhythms (pipeline, deal reviews, forecasting). Use conversion data to inform coaching priorities and performance management. Drive accountability while fostering a culture of ownership and continuous improvement.

What Success Looks Like

• Within the first 90 days, this leader will: Establish consistent and effective deal review cadence. Improve strategic clarity across active enterprise opportunities. Increase diagnostic rigor in discovery conversations. Strengthen pipeline coverage visibility and inspection. Bring structure and accountability to the enterprise sales motion.

• Over two quarters, success includes: Measurable improvement in conversion rates. Improved pipeline quality and coverage consistency. Reduced performance variance across reps. Greater predictability in forecasting. Hit the number.

Required Qualifications

• 7+ years of B2B SaaS sales experience, including significant enterprise selling exposure into 6 and ideally 7 figure deals.
• 3+ years managing Enterprise Account Executives in complex, multi-stakeholder environments.
• Proven ability to coach enterprise deal strategy and executive engagement.
• Experience building operating cadence in high-growth environments.
• Consistency in meeting and exceeding revenue and pipeline generation targets.
• Demonstrated ability to “figure it out”
• Located in the San Francisco Bay Area.

Alignment with Collectly’s GTM Values:

• We are owners - we have high ownership and take action.
• We is greater than me - we have humility and put the team first.
• We know our numbers - we are data-driven and understand how to impact our business internally and our customers’ business externally.
• We are AI powered - we automate easy repetitive tasks and research so we can solve harder problems and have a greater impact.
• We are one with the Buffalo - we expect that there will be challenges along the way and, like the Buffalo, we confront these challenges head on by running INTO the storm.

Core Competencies

• Strong enterprise qualification and deal strategy expertise (MEDDPICC, Challenger, GAP Selling, Selling through Curiosity).
• Ability to improve diagnostic quality in complex sales conversations.
• Data-driven mindset with strong pipeline and conversion analysis skills.
• High standards and comfort holding senior sellers accountable.
• Action-oriented leadership style with a focus on measurable outcomes.
• Ability to thrive in a dynamic start-up environment
• Deep curiosity and a strong Growth Mindset
• Experience with a modern sales tech stack

Preferred Qualifications

• Experience selling into healthcare providers or revenue cycle environments.
• Background in early stage venture-backed SaaS companies.
• Familiarity with AI-driven or workflow automation solutions.

Why You'll Love It Here

• Unlimited PTO: We believe in work-life balance and encourage you to recharge when you need it.
• Comprehensive Health Coverage: Fully paid medical, dental, and vision insurance for you and your dependents, because your well-being matters to us.
• Equity Opportunities: Share in our success with stock options - your hard work will drive our growth.
• Retirement Planning Made Easy: Enjoy a 401(k) with a generous company match to secure your future.
• Student Loan Support: We help lighten the load with contributions toward your student loans.
• Competitive Compensation: $330,000 - $390,000 per year on target earnings, plus equity.

If you think you’re a “Buffalo” who has what it takes to have a meaningful impact within our rapidly growing organization and to the broader healthcare industry - apply to come join our team today!