Senior Director of Onboarding

Rentvine • Bonita Springs, FL

11d • Hybrid

About The Position

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.

Requirements

• 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
• Track record of scaling output without proportional headcount growth

Nice To Haves

• Vertical SaaS or SMB-to-mid-market experience preferred; property management, real estate, or fintech a plus

Responsibilities

• 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.
• 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.
• Cost-to-serve modeling by segment and package.
• 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.
• 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.
• Scale throughput through process, tooling, and AI — not primarily through headcount.
• Lead and develop managers across both onboarding orgs; build the bench.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed