Chief Product Officer, Mainstay
$225-300k
+ Equity
More information about location
Chatbot-powered student engagement platform
Open for applications
Chatbot-powered student engagement platform
21-100 employees
Open for applications
$225-300k
+ Equity
More information about location
21-100 employees
Company mission
To help people take the next step toward a more fulfilling life.
Role
Who you are
- 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?
- 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
- 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
What the job involves
- 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
- 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
- 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
- This role reports directly to the CEO
Our take
Mainstay’s education-oriented chatbot uses the latest in AI to provide the guidance students need to navigate the college experience.
Colleges can’t always be there at all hours of the day to answer student questions. Mainstay’s system uses SMS text messaging, web chat, and chatbots to provide information and tailored, interactive messages to help drive enrollment. Given multiple randomized controlled trials that have demonstrated that Mainstay’s platform leads to increased enrollment, this is a valuable asset for any educational enterprise looking to maximize its investment.
A variety of colleges, including Wayne State, West Texas A & M, and Allegheny College have successfully used Mainstay’s system to increase enrollment, particularly for underserved populations. While Mainstay is continuing to establish itself given its recent name change from AdmitHub, and with competitors such as Intercom and Drift vying for a share in the college conversational sales market, Mainstay will need to continue to make the most of its recent $16 million investment to continue to provide education-enhancing services.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-6% employee growth in 12 months
Company
Company HQ
Downtown Crossing, Boston, MA
Leadership
Kirk Daulerio
(Co-Founder)They previously worked in athletics at their alma mater, Swarthmore College; on the admissions staff of Princeton University, University of Pennsylvania, and Bowdoin College; in college counseling at Gould Academy; and as Director of Member Relations for the Common Application.
Andrew Magliozzi
(Co-Founder & CEO)Before founding Mainstay (formerly AdmitHub) in 2014, they founded Signet Education and KarmaNotes.org. They have an undergraduate degree from Harvard College in History and Literature.
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