Chief Revenue Officer

Are you an entrepreneurial, intellectually curious, and energetic person?  Are you excited about working on new and exciting problems and driving large scale social impact?  Mainstay is looking for a Chief Revenue Officer who has built and scaled growth teams, thrives on collaboration, and brings a steady mix of strategic thinking and operational discipline.

Who We Are

At Mainstay we deeply care about the outcomes of our partners. We're an extension of their teams who work to understand their goals, strategic priorities and plans, and align our efforts to meet their needs as a true partner.  We use technology to scale the science of student success coaching through a communications platform that coaches students to and through college. We are a Public Benefit Corporation, with a commitment to helping more students access and achieve higher learning. We use human-centered, AI-enhanced coaching to proactively help learners find the answers they need, wherever they are, whenever they need it--and offer colleges a way to scale one-on-one support to their entire student body.

As Chief Revenue Officer, you’ll lead our go-to-market teams — including sales, marketing, and customer success. Reporting to the CEO and working closely with the VP of Finance and CPO, you’ll help shape and implement the strategies that drive sustainable revenue growth and expand our reach across education and workforce ecosystems.

You’ve led revenue and go-to-market teams in a B2B SaaS business — maybe in higher ed, maybe not — but you know how to build a system that works. You’re not looking for a rinse-and-repeat job. You want a challenge. You want to develop a team, drive real results, and help an organization get to the next level.

You know that winning is about getting the fundamentals right: clear strategy, strong leadership, good people, and staying close to the customer. You’re comfortable working across departments, rolling up your sleeves when needed, and helping a team do the best work of their careers.

What You’ll Do

• Build a clear, focused GTM plan that connects what we do to what our customers need
• Get sales, marketing, and customer success moving in sync
• Work closely with product, engineering, and finance to turn company goals into action

• Lead a cross-functional team — develop the leaders, support the doers
• Put systems in place so the team can operate with consistency and confidence
• Create a culture where people know what’s expected, get better every day, and take pride in their work

• Use data to see what’s working, fix what’s not, and stay ahead of the curve
• Find new product opportunities and keep the GTM engine running smoothly
• Make sure teams are aligned so the partner experience feels seamless

• Build strong relationships with institutional leaders and decision-makers
• Show up with clarity, insight, and a real understanding of how we help students and schools succeed

What You’ll Have

• 15+ years of experience leading go-to-market or revenue functions at a B2B SaaS company, driving sustainable growth over time
• Built and scaled teams across sales, marketing, and customer success — and worked closely with product, finance, and support
• Designed full-funnel strategies that connect lead gen to retention, with metrics and accountability at every step
• Balanced strategy with execution — knowing when to step back, and when to dive into the details
• Used data to make decisions, coach teams, and constantly improve performance
• Created a culture that rewards ownership, follow-through, and improvement over perfection
• Experience leading teams through ambiguity, innovation cycles, and rapid change
• A collaborative mindset — you work well with visionary founders, cross-functional teams, and external partners leading with with clarity, humility, and strong communication and a belief that alignment is more powerful than control
• You take the work seriously, not yourself

This role reports directly to the CEO. Remote candidates within the U.S. are welcome. Occasional travel to Boston and partner sites is expected.

Mainstay is committed to creating a company where all employees regardless of background can show up and feel they belong. This is an ongoing journey, and we welcome questions on where we’re at during your interview process. We are proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or fitness level.

The pay range for this role is $305k to $425k depending on the level you’re hired at. Actual compensation packages are based on a wide array of factors unique to each candidate including but not limited to demonstrated skill set, years & depth of experience, and some role dependent factors that can include certifications and software expertise. We also hope you’ll consider and be open to what else we provide outside of our base compensation. This includes our benefits, perks, equity, and other aspects of our overall employer brand including our culture which is built on our mission, vision and values.  We welcome direct conversations with each candidate about compensation in all our initial calls.