About the role
About OpenLoop
OpenLoop was co-founded by CEO, Dr. Jon Lensing, and COO, Christian Williams, with the vision to bring care anywhere. Our telehealth support solutions are thoughtfully designed to streamline and simplify go-to-market care delivery for companies offering meaningful virtual support to patients across an expansive array of specialties, in all 50 states.
About the Role
OpenLoop's mission is to bring care anywhere by powering telehealth solutions at scale. We empower any brand, individual, or organization to launch compliant virtual care in weeks, not months.
We're hiring a Senior Director, Employer to build and scale our employer vertical. This is a senior, strategic role responsible for generating pipeline, closing complex deals with self-insured employers, and developing the broker and benefits-consultant relationships that drive access to this market.
You will own how OpenLoop wins with employers—directly and through channel—selling clinical solutions that reduce total cost of care and improve outcomes for employee populations. This is a builder's role for someone who understands the employer benefits buying process and wants to own a vertical.
What You'll Do
- Own employer revenue end to end—build, manage, and grow a pipeline of self-insured employers, and carry the number for the vertical.
- Lead complex, multi-stakeholder sales cycles involving benefits, HR, finance, and executive buyers, navigating a procurement process that often runs through brokers and consultants.
- Develop and manage relationships with benefits brokers and consultants as a core route to market, ensuring OpenLoop is positioned and recommended in employer evaluations.
- Position OpenLoop's clinical solutions as a lever to reduce total cost of care and improve outcomes—starting in clinical nutrition and medical weight loss, and expanding into additional specialties.
- Build the go-to-market and operational infrastructure—playbooks, pricing approaches, and reporting—that move the vertical from early deals to a repeatable, high-growth revenue stream.
- Navigate the annual benefits cycle, aligning your pipeline and close timing to open enrollment and plan-year decision windows.
- Work cross-functionally to ensure clinical, product, operations, and customer support are informed and aligned ahead of every employer implementation and launch.
- Other duties as assigned.
Who You Are
- 10–15+ years of B2B sales or business development experience, with significant time selling clinical, benefits, or point solutions into self-insured employers.
- Deep fluency in the employer benefits ecosystem—self-insured plan design, total cost of care, and the annual enrollment cycle.
- Established relationships with benefits brokers and consultants, and a clear point of view on how to win through channel.
- A proven closer of complex, multi-stakeholder deals with long sales cycles across benefits, HR, finance, and executive buyers.
- You build the machine, not just the deal—you are comfortable creating the playbooks, systems, and structure a vertical scales on.
- You thrive in ambiguity and build your own structure when the playbook does not exist yet.
- You have hands-on experience with HubSpot or a similar CRM and maintain accurate, current pipeline data and honest forecasting.
Our Benefits
In addition, for salaried positions you would also be eligible for:
- Medical, Dental, and Vision plans
- Flexible Spending/Health Savings Accounts
- Flexible PTO
- 401(k) + Company Match
- Life Insurance, Pet insurance, and more
Our Company
We have a relatively flat organizational structure here at OpenLoop. Everyone is encouraged to bring ideas to the table and make things happen. This fits in well with our core values of Autonomy, Competence and Belonging, as we want everyone to feel empowered and supported to do their best work.
Sound like a good fit? We’d love to meet you.