Director of Commercial Success

Millions of patients skip the care they need for one reason: they can't figure out how to pay for it. Wellfit exists to erase that barrier. As a pioneering healthcare fintech company, we're rebuilding how patients, providers, employers, and payors handle the cost of care, and we're doing it in an industry that has waited decades for someone to get it right. This is the mission you would make every field sales representative ready to sell. We're hiring a Director of Commercial Success to build the operating engine behind our field sales team. Reporting to our SVP of Sales & Revenue, you'll own how field sales representatives are onboarded, trained, and equipped, plus the systems and data that keep the motion running as Wellfit shifts toward a payments-centric future. This is an individual contributor role with no direct reports. You won't carry a quota and you won't manage the field sales team; you'll make them faster, sharper, and less blocked. 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, as a trusted advisor and advocate rather than a manager. Performance management stays 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 the CRM, Microsoft Dynamics today, end to end. Keep the data clean, the pipelines accurate, and the team fluent in using it. You surface and report on pipeline health upward; you are not accountable for 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 the playbooks, talk tracks, and enablement content that turn our payments story into closed deals across dental, medical, and new verticals. • Clearing the path: Put out fires internally so the field keeps selling. When a representative hits an obstacle, you navigate the internal teams and get it unstuck. • 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 them, decision them, and hand off a clear scope of work rather than letting every request land on marketing directly. • Measurement: Define the 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 the readiness, systems, and support the team needs to execute it. 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: • An operator first. Exceptionally organized, buttoned up, and comfortable owning the details most salespeople would rather avoid. • Someone who can coach and advocate for a team they don't manage, and earn the influence instead of relying on a title. • Someone with backbone. Measured, direct, and confident holding a high standard. • Comfortable as a strategic right hand, amplifying a senior leader's strategy rather than seeking the spotlight. • A systems thinker who turns one-off wins into repeatable programs. • A strong communicator who can 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. • A 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, and 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 the company bonus program. This is not a commission-carrying role. Wellfit Perks and 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.