Director of Commercial Success

About the role

Wellfit exists to erase the barrier that keeps millions of patients from getting the care they need. As a pioneering healthcare fintech company, we’re rebuilding how patients, providers, employers, payors, and field sales representatives handle the cost of care. Reporting to the SVP of Sales & Revenue, the Director of Commercial Success will build the operating engine behind our field sales team: onboarding, training, systems, and data that make the motion repeatable and scalable as Wellfit shifts toward a payments-centric future. This is an individual contributor role with no direct reports and no quota.

What You’ll Own

• Onboarding and ramp: Build and run the new-hire program for field sales representatives from the ground up, then maintain it as the team grows.
• Training and coaching: Deliver ongoing training and skills coaching that lifts the whole team, acting as a trusted advisor and advocate rather than a manager; performance management remains with sales leadership.
• Sales methodology: Introduce and embed a modern, consistent sales methodology so the team sells the same disciplined way, working through sales leadership to make it stick.
• CRM ownership: Own Microsoft Dynamics end to end—keep the data clean, pipelines accurate, and the team fluent; surface and report on pipeline health upward without owning the numbers themselves.
• Single source of truth: Own and maintain the go-to home for sales enablement content currently spread across Ignite and elsewhere so the field always knows where to look.
• Playbooks and content: Create playbooks, talk tracks, and enablement content that turn Wellfit’s payments story into closed deals across dental, medical, and new verticals.
• Clearing the path: Navigate internal teams to remove obstacles so the field keeps selling.
• Liaison to product: Serve as the connective tissue between sales and product, carrying field signal into the roadmap conversation and bringing answers back.
• Liaison to marketing: Be the front door for sales requests into marketing—intake, triage, and hand off clear scopes of work instead of letting every request land directly on marketing.
• Measurement: Define enablement KPIs (ramp time, win rates, quota attainment) and use them to prove impact and refine every program.
• Operational partnership: Act as the operational right hand to sales leadership, translating sales strategy into readiness, systems, and support the team needs to execute.

What Success Looks Like

• New field sales representatives ramp faster and hit quota sooner than they do today.
• A consistent, repeatable sales motion replaces ad-hoc, individual selling.
• Sales, product, and marketing move through one clear channel instead of ad-hoc requests in every direction.
• CRM data is clean and trusted, and pipeline reporting is something leadership can act on.
• The team can confidently sell Wellfit’s payments solutions into new verticals: dermatology, med spa, veterinary.
• Enablement is measured and trusted as a driver of revenue, not a cost center.

Who Thrives Here

• Operator first: Exceptionally organized, buttoned up, and comfortable owning the details most salespeople would rather avoid.
• Coach and advocate: Able to coach and advocate for a team you don’t manage and earn influence without relying on a title.
• Backbone: Measured, direct, and confident holding a high standard.
• Strategic right hand: Comfortable amplifying a senior leader’s strategy rather than seeking the spotlight.
• Systems thinker: Turn one-off wins into repeatable programs.
• Strong communicator: Influence and align across sales, marketing, and product.

Must-Haves

• 10 to 12+ years of experience in sales enablement, sales operations, sales leadership, or a closely related role.
• Payments, fintech, or healthcare payments background.
• Proven track record building onboarding, training, and coaching programs that measurably improved sales performance.
• Hands-on CRM ownership, ideally Microsoft Dynamics or comparable, including data hygiene, pipeline reporting, and driving adoption.
• Experience implementing and embedding a modern sales methodology across a team.
• Strong command of enablement metrics (ramp time, win rate, attainment) and the ability to prove program ROI.
• Excellent communication and cross-functional influence, especially partnering with senior sales leaders and with product and marketing.

Nice-to-Haves

• Prior quota-carrying experience as an AE, AM, or sales manager for firsthand insight into what the field actually needs.
• Familiarity with the dental industry or provider-facing sales.
• Experience standing up an enablement or sales operations function from an early or unstructured state.
• Bachelor’s degree in Business, Marketing, or a related field.

Compensation

Competitive base salary plus participation in the company performance bonus program. This is not a commission-carrying role.

Benefits

• Company Bonus: Participation in the company performance bonus program.
• Comprehensive Health Coverage: Medical, Dental, and Vision.
• Unlimited Paid Time Off: With a supportive culture that encourages you to take it.
• 401k: With up to 4% match, helping you invest in your future.
• Flexibility: A remote-friendly culture with travel as needed.

Wellfit may use artificial intelligence tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals based on available information. These tools assist the recruitment team but do not replace human judgment; final hiring decisions are made by humans.