Chief Revenue Officer


Job Description

For this role, coming at this particular phase in our life cycle, we think a little more context would be helpful.  We are the undisputed market leader in open enrollment benefits decision support, thanks to 1600+ unbelievable customers.  However, we’re not resting on those laurels.  We’re actively pushing from helping employees *choose* benefits, to helping them *use* benefits any time during their moments of need.  Our mission is to help employers measurably reduce the cost of benefits confusion -- and with $1.3 trillion or so of annually recurring spend, of which C-suite executives believe 53% is wasted due to employee confusion, we have our work cut out for us and are facing a number of transformations:

  • We’re evolving from a single product company to a platform company with an expanded portfolio of value provided to customers , so we need a CRO who can handle complex SaaS sales.
  • Our “customer base” includes not only employers and their employees who use our software, but also the complex web of carriers, consultants, brokers, and point solution providers (our channel and alliance partners), so you’ll need to help us structure a collaborative, communicative team approach that is steeped in all aspects of our industry and the perspectives and needs of all the constituents we serve, and do so as efficiently as possible.
  • Our platform is increasingly reliant on personal data and integrations, so we need a CRO who is comfortable “talking tech,” and helping a team of sellers guide customers through both technical and non-technical conversations,  overcoming objections and providing the assurances our customers need for us to do our jobs well.
  • Even before Covid, our buyers were increasingly educating themselves about the industry since we’re dealing with such big and well established pain (benefits confusion), so we need a student of industry, someone who deeply cares about learning and serving customer needs in the most helpful way possible, and will experiment with staff, structure, automation, and approach to continually improve.  

How you’ll help

The Chief Revenue Officer will report to the CEO, serve on the Executive leadership team, and will be responsible for driving revenue for the company from customer and partner acquisition through growth and expansion perspective.  In short, you’ll be responsible for Company’s go to market plan, staff, and playbook for maximizing revenue and long-term value creation.  In longer:  

  • Growth.  You’ll define strategies for growth, open new paths to revenue, and will work with our product team to make sure we’re bringing valuable solutions for real customer pain.
    • You’ll direct leaders to source new opportunities as delightfully and efficiently as possible, often talking about a well known business (ours) in new ways.
    • You’ll direct leaders to win and onboard customers with the right mix of features to maximize our revenue AND the customer’s chances of seeing success/value.
    • You’ll direct leaders that plan account by account for mutual long-term success and growth. 
  • Organizational Development.  You’ll evolve our organization to make sure we’re serving the needs of both employers and strategic partners as efficiently and effectively as possible.  You’ll guide the organization in designing and implementing annual targets and talent strategies so that everyone on the team feels smarter, more effective, and well rewarded for their contributions here.  
  • People.  You’ll help us find, retain, coach, and grow a team of strategic, kind, and helpful revenue executives who believe that business is a team sport and our customers are best served by listening, truth telling, collaboration, and solving real problems humbly and with no BS.  You’ll set a standard for what “great performance” looks like for all of your departments and hold all managers accountable for rigorous standards of feedback, performance benchmarking, and reorganizing as needed to better serve the needs and goals of the business. 
  • Alignment.  You’ll be a trusted thought partner to the CEO and senior leadership team who believe that salespeople can be helpful, delightful, strategic, customer-focused, and a pleasure to work with.  You’ll tell us what the market wants and needs and know when there’s a difference, and you’ll help us all row in the right direction.  You’ll optimize our GTM strategy in terms of direct, channel, and marketing.
  • Plan for the Future.  You’ll use both data and your gut to make the unknown as predictable as possible.  You’ll anticipate and remove blockers from both the grand vision and your team’s annual goals.  You’ll help make our customers and partners glad for a world with Company in it.
  • Build in All Ways.  You’ll help us assess and integrate potential acquisitions, building cohesive, additive new culture when we decide to buy vs build.
  • We’re looking for someone who wants to be a real partner to peers and a valued  executive team member who is interested and willing to contribute to the business, even if it’s “outside your lane.”

Experience & skills you’ll need

  • 15+ years of experience leading Revenue organizations (sales, sales development, and account management); must have experience balancing channel and direct teams.
  • 10+ years experience in both SaaS and healthcare/benefits technology sales
  • Experience in growth stage tech companies, and with partially distributed workforces with employees in multiple states
  • Experience with integrating acquisitions a huge plus
  • Ability to write and communicate in “human” versus corporate jargonese
  • Experience implementing an approach for expanding customer relationships to more senior stakeholders, especially CHRO and CFO buyers
  • Experience working in an industry where third party sources of funding and channel influence are important.  
  • Ability to lead with trust and benefit of the doubt, because our people have earned it
  • Forward-looking approach with the expectation to win without letting the small stuff (or the big stuff) get you down
  • A sense of humor, because it makes the days more enjoyable, and is a huge part of what and how we sell and engage our users.
  • Experience with forecasting across multiple channels will really come in handy..  
  • Experience with creative approaches to monetization or experiments with new monetization models a big plus.  
  • Experience selling in a context where significant expanded value is being offered and so everything from the lead gen to the standard pitch to the demo needs to be expanded in scope and a broader story about value needs to be told


  • Drives Results –  we’re builders and try-ers, who use both data and gut to make decisions, and want the same in our CRO.  But let’s be clear:  we really like math and expect ROI based decisions.
  • Attracts Top Talent –  you’ll be both a leader and a player coach, and it would be great if you could help us add more industry expertise to our team.
  • Strategic Mindset – you can build a robust business case, make a gut call, and know when each is required.
  • Customer Focus - we seek and tell the truth with kindness and respect; the more we truly understand what our customers' pains and priorities, the more quickly we will solve for them.
  • Drive Team Engagement - yes, we need a strong bottom line-orientation with a track record of exceeding goals successfully.  But so too do we need someone who can motivate and inspire our people, and make it fun along the way.  You will be a steward in both maintaining and evolving our awesome culture here.  Your team should value the time they spend with Company and know that they’re both better thinkers and performers and more valuable in the market for it.
  • Cultivates Innovation – we’re not looking for “standard and basic” strategies.  We’re looking for someone with tons of ideas and the ability to test and try things, someone who asks “could we” because more often than that we can, and we will, try new things that help us support our people while growing our business.
  • Ensures Accountability - we’re serious about doing what we say we will, so we’re looking for someone with a strong sense of ownership who’ll  establish clear responsibilities and processes for monitoring work and measuring results
  • Lastly, while we don’t take ourselves too seriously, we’re dead serious about integrity and treating our customers’ time and money with the respect they deserve.  We don’t cut corners ever just to get a deal, but rather play the long game, customer by customer, partner by partner, employee by employee.

Job Requirements