Head of Mergers and Acquisitions

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. #J-18808-Ljbffr Daisy