Jobs at Alumni Ventures Portfolio Companies


Regional VP of Sales



Sales & Business Development
Canada · United States · Remote
Posted on Wednesday, March 27, 2024

OfferFit was founded by ex-McKinsey and BCG math PhDs, and we’re funded by leading Silicon Valley VCs. OfferFit replaces A/B testing with automated experimentation, powered by self-learning AI. This allows lifecycle marketers to test & improve the performance of their campaigns much faster than before. Customers include leading brands like Brinks Home, Yelp, Engie, and MetLife, among many others.

Note for Applicants:

Data shows that men on average apply for a role if they meet 6/10 requirements while women often only do so if it’s 10/10. We work hard to be clear and specific about what our roles require, and we encourage you to apply even if you don’t check all the boxes! Applying gives you the opportunity to be considered and we look forward to reviewing your application!

Position Overview:

We're expanding our sales team rapidly and seeking a Regional Vice President to join us! In this role, you'll lead a team of Account Executives (Directors of Strategic Accounts), providing robust coaching and management support to facilitate our ongoing growth. Reporting directly to the VP of Sales, you'll play a pivotal role in our scaling efforts.

Responsibilities include:

  • Coach the team on sales best practices and OfferFit’s end-to-end sales process (from prospecting through to negotiation & close)
  • Support your team in defining the strategy for key deals and working through deal roadblocks
  • Participate in critical sales calls (e.g., proposal meetings)
  • Forecast with accuracy
  • Recruit, develop, and retain a top-performing team of sales professionals
  • Contribute your perspective & experience to shaping OfferFit’s overall GTM strategy

Why this job is great?

  • Build an industry-defining company – OfferFit is on a mission to replace A/B testing with AI testing. When we succeed, this will redefine the marketing profession – something we will all look back on with pride.
  • Be on an exceptional leadership team – Our leadership team is full of talented, collaborative people who support each other and genuinely enjoy working together; our founders are experienced entrepreneurs with math PhDs and McKinsey/BCG experience.
  • Be part of a strong culture – We have very high employee satisfaction; we’re an all-remote global team but gather in person once a quarter; our culture is demanding & meritocratic, but also warm and supportive.
  • Be set up for success – OfferFit has raised ~$50m from leading VCs (including Menlo Ventures, Canvas Ventures, and more) and has been growing quickly (e.g., ~3x in 2023).

Who's a fit?

  • Excellent people leadership skills, including ability to attract and retain top talent
  • Strong enterprise sales skills: prospecting, discovery, qualification, negotiation, etc.
  • Strong business & financial acumen: ability to speak as a peer with C-level buyers at large enterprises
  • Excellent collaboration skills: ability to work collaboratively with colleagues in business development, marketing, customer success, finance, and product


  • Sales for a hypergrowth enterprise SaaS company with high ACVs (>$100k)
  • Proven ability to build and manage growing sales teams. Track record of instilling a positive culture to achieve results with accelerated delivery
  • Communicating about technically complex products to both technical and non-technical buyers
  • Fluency with MEDPICCR
  • Experience with value selling methodologies (like SPIN Selling, Challenger Sale, Command of the Message, etc.)
  • Exposure to machine learning / AI and marketing technology / “front-office” software is a plus

The base salary range for this position in the United States is $174,000-$192,000 per year, plus eligibility for additional commission/bonus ranging $204,000-$222,500, with an overall OTE of $378,000-$414,500 (ability to earn more based on sales goals); Eligibility for an additional end of year performance bonus, commissions (when applicable) and/or equity options may be provided as part of the compensation package, in addition to a full range of medical, financial, and/or other benefits, depending on the position offered. For non-US based candidates, base pay and overall compensation packages will be adjusted based on location. Applicants should apply via OfferFit’s internal or external careers site.

OfferFit Benefits and Perks:

  • Generous PTO (starting at 25 days PTO per year) and Parental leave policy (12 weeks paid)
  • 100% remote work environment with flexible hours
  • Quarterly gatherings where we meet in person in a different city to work together, bond as a team and celebrate our progress
  • Weekly team events (lunch and learns, trivia, virtual escape rooms, town hall and team health “barometer” meetings)
  • Ability to learn and develop from an experienced leadership team (ex-Amazon, McKinsey, BCG, and IBM, among others) who are focused on building a talented, diverse, and inclusive tea
  • Dedication to building a strong culture (e.g., team resource groups, weekly recognitions, major life event celebrations, mental health/sustainability days off, etc.)
  • [US Only] Competitive benefits (major medical, vision, dental and LTD) and 401K matching program

OfferFit is committed to a diverse and inclusive workplace. OfferFit is an equal opportunity employer and does not discriminate on the basis of race, national origin, gender, gender identity, sexual orientation, protected veteran status, disability, age, or other legally protected status.