Senior Director of Onboarding

Job Title:

Senior Director of Onboarding
Location: On-site (preferred) in Bonita Springs, FL. Open to remote candidates inTampa, FL, Miami, FL, Orlando, FL, Fort Myers, FL, Atlanta, GA
About Rentvine
Rentvine is the fastest-growing property management software company in the industry, ranked #60 on the 2025 Inc. 5000 list. Our powerful, cloud-based platform helps property managers streamline operations, reduce manual work, and deliver a better experience for tenants and owners. Behind that innovation is a team-first culture that puts people at the center. We care deeply about building a company where smart, driven individuals can grow, feel supported, and do the best work of their careers. Our people aren't just part of our success—they're the reason for it.
Please Note: Rentvine is unable to provide employment sponsorship now or in the future for this position. Candidates MUST currently reside in the USA to be considered.
About the Role
Rentvine is property management software built for property managers. Onboarding is where a customer's decision to switch becomes real — data migrated, systems configured, portfolios live, website built. We're hiring a Sr. Director to lead onboarding across our product lines and to own how onboarding is scoped, priced, and packaged. You'll run implementation delivery end to end, and you'll own the commercial model behind it: service tiers, pricing, SOWs, and cost-to-serve.
It's a builder's seat. The teams and the customers are already here. The operating model and the services architecture are yours to design.
What You'll Own
Onboarding delivery for Rentvine and PMW.

One team, one model. Data migration, configuration, and technical go-live across both products, including the integration of two teams into a single operating structure.
Time-to-live.

Own the implementation timeline through go-live and the handoff into customer education, who takes the customer from live to proficient. Move faster without trading away the quality that drives our retention.
Implementation economics.

Cost-to-serve modeling by segment and package.
Pricing and packaging for onboarding.

Design the tiers, define what's included versus scoped, and set the pricing model. Partner with Finance and Sales on approval thresholds and margin targets.
Scoping and SOWs.

Author the SOW framework, run the scope approval workflow, and be the escalation point on non-standard deals. Keep Sales fast without letting scope walk.
Capacity and efficiency.

Scale throughput through process, tooling, and AI — not primarily through headcount.
The team.

Lead and develop managers across both onboarding orgs; build the bench.
Qualifications
10+ years in professional services, implementation, or onboarding, with 5+ leading leaders in a B2B SaaS environment
Direct experience owning a services P&L or cost-to-serve model — you can talk about margin, utilization, and scope creep in specifics
Built or meaningfully reshaped a pricing and packaging model for services, not just executed against someone else's
Comfortable writing and negotiating SOWs, and setting the guardrails others work inside
Has integrated teams post-merger or post-reorg, and can speak to how they handled the people side
Data migration fluency — enough to be credible with the technical team and honest with the customer
Runs clean handoffs across functions — you've owned a stage in a lifecycle, not a silo, and can partner with an education team you don't control
Vertical SaaS or SMB-to-mid-market experience preferred; property management, real estate, or fintech a plus
Track record of scaling output without proportional headcount growth
Location / Travel Requirements
This role is based on-site at our Bonita Springs, FL office, which is our preferred setup.
We're also open to remote candidates based in one of these metro areas:

Tampa, FL
Miami, FL
Orlando, FL
Fort Myers, FL
Atlanta, GA

Remote hires will travel to our Bonita Springs office once a month for 3-5 days

to work in person with the rest of the leadership team. This is a recurring requirement, not occasional. All travel expenses are covered.

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