Chief Revenue Officer, Mainstay
$305-425k
+ Equity
More information about location
Chatbot-powered student engagement platform
Open for applications
Chatbot-powered student engagement platform
21-100 employees
Open for applications
$305-425k
+ 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?
- 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
- 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
What the job involves
- 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
- 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
- Set and Execute Go-to-Market Strategy:
- 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
- Build and Strengthen the Team:
- 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
- Drive Sustainable Growth:
- 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
- Represent Mainstay in the Market:
- 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
- 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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