Chief Product 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 Product Officer who can simplify complexity, move fast in ambiguity, and build trust with CIOs and students alike. This is more than a product role — it’s a chance to shape the future of higher education with AI.

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.

You’ll be the thought partner to our CEO, helping refine bold ideas into scalable strategies. You’ll lead cross-functional teams across product, engineering, expert services, conversation strategy, and support — ensuring Mainstay’s solutions are simple, secure, and deeply impactful for our users.

We’re looking for someone who knows how to connect vision to execution. You’ll lead with purpose, partner with top institutional leaders, and drive Mainstay’s next phase of innovation.

What You’ll Do

Set the Vision & Strategy

• Define and drive a unified product and technology strategy aligned with Mainstay’s mission and business goals
• Collaborate with the CEO to shape and test bold ideas — then translate those into roadmaps and outcomes
• Identify and invest in the right technologies and platforms to scale impact, efficiency, and innovation

Lead Cross-Functional Execution

• Oversee the full product lifecycle — from discovery to delivery — across product, engineering, expert services, support, and AI conversation strategy
• Work closely with sales, marketing, and partner success to ensure cohesive product launches, positioning, and messaging
• Drive adoption of user-centered design principles and continuous improvement 

Strengthen Technical and Operational Foundations

• Modernize and scale our technical infrastructure, including data pipelines, platform architecture, and GenAI capabilities
• Ensure strong security and compliance practices — including owning our SOC 2 certification process and representing Mainstay’s cybersecurity posture with institutional CIOs
• Lead build-vs-buy decisions with a clear understanding of market landscape, vendor capabilities, and long-term cost/value tradeoffs

Build a Data-Driven Culture

• Develop and implement a clear data strategy to surface actionable insights across the student journey
• Partner with other leaders to use data to improve student outcomes, partner success, and internal decision-making
• Make data accessible and impactful across the org with thoughtful tools, training, and storytelling.

Inspire and Develop Talent

• Lead and mentor a multidisciplinary team of engineers, product managers, conversation strategists, and service leaders.
• Foster a culture of experimentation, accountability, and purpose.
• Attract and retain mission-driven talent that wants to make a real difference in education.

What You’ll Have

• 15+ years of experience across product, engineering, or hybrid leadership roles — with a proven ability to scale secure, intuitive platforms.
• Deep understanding of cybersecurity and compliance frameworks, with experience owning conversations with CIOs and IT leaders.
• Strong product intuition, with a track record of simplifying user experiences and launching impactful features.
• A collaborative mindset — you work well with visionary founders, cross-functional teams, and external partners.
• Experience leading teams through ambiguity, innovation cycles, and rapid change.
• A passion for using technology to drive social impact — especially in education, workforce, or coaching.

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 for this role is $225k - $300k 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.