10+ years in professional services, implementation, or onboarding, with 5+ years in leadership roles in a B2B SaaS environment
Experience managing a services P&L or cost-to-serve model, with a focus on margin and utilization
Proven track record in developing pricing and packaging models for services
Skilled in writing and negotiating SOWs, establishing operational guardrails
Experience integrating teams post-merger or reorganization, with a focus on team dynamics
Fluency in data migration processes to effectively communicate with technical teams and clients
Ability to manage cross-functional handoffs and collaborate with education teams
Preferred experience in vertical SaaS or SMB-to-mid-market sectors, particularly in property management, real estate, or fintech
Demonstrated ability to scale operations without proportional headcount increases
Responsibilities
Lead onboarding delivery for Rentvine and PMW, integrating teams into a unified model
Own the implementation timeline from start to go-live, ensuring quality and speed
Model implementation economics, focusing on cost-to-serve by segment and package
Design and define pricing and packaging for onboarding services, collaborating with Finance and Sales
Author and manage the SOW framework, ensuring scope approval and fast Sales processes
Enhance capacity and efficiency through process improvements and technology, rather than increasing headcount
Develop and lead managers across onboarding teams, building a strong leadership bench
Benefits
Onsite/hybrid work model at the Bonita Springs, FL office
Remote work options available for candidates in select metro areas
Monthly travel to the Bonita Springs office covered for remote hires
Collaborative leadership environment with a focus on team development
Full Job Description
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 onsite/hybrid 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, FL 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.
