Key skills
AINegotiation
About this role
Description
About Us:
Daisy is building the future of living. As a full-stack, AI-native property management company for HOAs, co-ops, and condos, we're modernizing one of real estate's largest and most fragmented industries. By combining technology with exceptional service, we deliver greater transparency for boards, more efficient operations, and a better resident experience.
In just a few years, we've become the 8th largest property management company in NYC, expanded across the tri-state area, and now manage over 5,000 units and $200M+ in building budgets.
Backed by strong growth and recent financing, we're entering our next chapter of growth as we expand Daisy's AI-powered operating model nationwide.
Overview:
We're hiring a Head of M&A to build and execute Daisy's acquisition strategy as we scale toward becoming the national leader in AI-powered property management. Reporting directly to the CEO, you'll work closely with the board and cross-functional leaders to shape strategy, source and close acquisitions, build integration playbooks, and create a repeatable M&A engine.
This is more than acquiring revenue or EBITDA; we're investing in customer relationships, local expertise, talented teams, and operating platforms that become stronger within Daisy's AI-native model. We believe the future of property management isn't just consolidation, it's transformation.
With an active acquisition pipeline, AI-powered sourcing capabilities, strong investor backing, and proven operating momentum, the foundation is already in place. We're looking for an experienced operator-investor to turn that momentum into a scalable acquisition platform by building trusted seller relationships, executing thoughtful deals, and creating a disciplined system for sourcing, underwriting, integrating, and growing acquired businesses.
What You’ll Do:
- Shape acquisition strategy with the CEO and board: target markets, segments, the deal sweet spot, and the sequencing of platform and tuck-in acquisitions.
- Build and run the proprietary sourcing machine: target database, owner enrichment, structured outreach, and pipeline tracking, powered by Daisy’s AI-native tools.
- Own deals end to end: sourcing, diligence, valuation, structuring, negotiation, closing, and a clean handoff into integration.
- Build the underwriting: standalone performance plus the margin bridge from acquired economics to Daisy’s AI-native model, with disciplined entry-multiple judgment.
- Partner with Finance and external capital providers on acquisition financing, including debt facilities and structured capital, and help build Daisy’s capital-markets capability.
- Earn trust with founders and owners: you are often the face of Daisy in the acquisition process, and credibility is what wins deals in this industry.
- Design the integration and retention plan with Operations, Product, and Technology, and protect the acquired revenue base through the critical post-close window.
- Track every deal against its thesis: margin curve, community retention, and variance to the underwriting case.
- Build the repeatable system: playbooks, templates, diligence standards, operating rhythms, and the team itself as volume grows.
What You Bring:
- 5–8+ years in private equity, investment banking, corporate development, or lower-middle-market M&A, with a track record of owning deals, not just supporting them.
- The judgment and presence to operate with a CEO and board, and to lead a function you will build from the ground up.
- Strong financial modeling, valuation, and structuring skills, with the ability to underwrite operational upside, not just current performance.
- Commercial instinct and real curiosity about how businesses run, plus the ability to find the true drivers and risks in messy data.
- Exceptional relationship skills with founders, owners, advisors, lenders, and internal teams.
- High ownership, low ego, strong execution, and comfort moving fast while the machine is still being built.
- Clear writing and judgment: you turn complex analysis into simple, decision-ready recommendations.
- Fluency using AI to accelerate sourcing, diligence, and execution.
Nice to Have:
M&A experience in real estate services, property management, HOA, condo or co-op management, or other fragmented, recurring, local-service industries.
Experience with roll-up or buy-and-build strategies, and with post-merger integration or operational value creation.
Familiarity with acquisition financing: senior debt, structured capital, lenders, family offices, and PE partners.
Compensation:
The salary range for this position is $200,000–$250,000 base salary, depending on experience and qualifications. Along with potential performance-based incentives, equity, and a competitive benefits package.