About the Role

What you'll do

• Conduct a comprehensive product audit and acquisition readiness assessment within the first 30 days
• Identify, prioritize, and execute warm introductions to strategic acquirers including enterprise HCM platforms, ATS vendors, and HR tech investment arms
• Advise on product roadmap gaps and customer usage narratives that strengthen acquisition appeal
• Develop and refine external-facing materials (one-pagers, pitch decks, positioning docs) for buyer conversations
• Represent Cantaloupe at relevant industry conferences and networking events (e.g., HR Tech, Unleash)
• Provide ongoing intelligence on competitive landscape, acquirer appetite, and deal timing
• Guide the founding team through deal structuring, diligence preparation, and negotiation strategy

What we're looking for

• 15+ years in the HR technology industry in a senior strategic, product, or business development capacity
• Demonstrated M&A experience — either as an advisor, acquirer, or founder who has navigated a successful exit
• Active, senior-level relationships with decision-makers at major HCM/ATS platforms (e.g., UKG, Workday, ADP, SuccessFactors, Cornerstone)
• Deep understanding of the talent acquisition and workforce management software landscape
• Proven ability to position early-stage products for strategic sale
• Strong executive communication and stakeholder management skills

Nice to have

• Prior experience advising or investing through an HR tech accelerator or venture arm (e.g., ADP Ventures)
• Familiarity with the QSR, hourly workforce, or frontline employee segment
• Existing relationships with emerging acquirers in the space (e.g., Darwin Box, iCIMS, Phenom)
• Conference presence and visibility at HR Tech, Unleash, or similar events
• Experience advising on asset sales specifically (vs. full company acquisitions)
• Prior CHRO network or credibility as an industry thought leader