The Situation
When I joined ResMan in 2021, comprehensive platform redesign had been discussed for years without happening. Over a decade of accumulated technical debt, engineers building duplicate solutions instead of shared libraries, and the investment required had prevented progress. Sales teams said our dated visual presentation hurt us in competitive deals. Many believed it would never get funded.
"Many believed it would never get funded."
The Challenge
The fundamental challenge was getting the funding and organizational commitment to actually do it — without a mandate, a budget, or a guarantee it would ever happen. Rather than wait for perfect conditions, I started building the foundation.
The Foundation (2021)
I conducted 60+ interviews across the entire organization and external customer base. I spoke with C-suite, department leaders and their teams, technical leads, customer success, support, sales, and customers to understand what each group wanted, what worked, and where gaps existed.
"Evolve intelligently, don't start over."
I documented everything in detailed notes, synthesized findings into a 40,000-word analysis, then condensed it to a 2,000-word executive summary supported by detailed documentation. The research revealed our path: evolve intelligently, don’t start over. Keep what users loved, improve what frustrated them, add what the market wanted.
The Work (2022 - 2024)
I led multi-year partnerships with our Customer Advisory Board and full-scale Boardroom redesign. Deep collaborative work uncovered calculation inconsistencies even our support teams hadn’t identified. We consolidated redundant modules, added data visualization for at-a-glance insights, and enabled ad-hoc property group viewing. Customers kept asking: “When can we get this?”
"Customers kept asking: 'When can get this?'"
When internal teams identified features they wanted to remove to simplify the platform, CAB feedback revealed several were essential to user workflows. Customer insight prevented costly mistakes. Throughout this period, I simultaneously led other high-stakes initiatives including Bulk Renewals. When a designer left the team without replacement funding, we absorbed her responsibilities and kept delivering.
The Opening (2025)
By 2025, ResMan’s parent company Inhabit secured Blackstone funding that made resources available. CEO Janel Ganim asked me to scope the redesign for a potential board presentation. I advocated for in-depth scoping beyond initial quick-analysis expectations. Janel agreed. I led detailed product analysis with our engineering team across every section — accounting, leasing, reporting, maintenance — scoring features using effort, uncertainty, and complexity criteria. I insisted on realistic timeline projections because board funding required achievable milestones. We conducted thorough risk analysis: engineer turnover likelihood and mitigation strategies, technical dependencies that could cause delays, project continuity plans. I recommended a phased funding approach to Janel: identify the initial phase with clear milestones, demonstrate success, then return with better information for subsequent phases rather than asking the board to approve detailed multi-year plans when variables would inevitably change.
The Outcome
Janel took the foundation and created the board presentation. Her influence and skill working with the board and organization turned four years of preparation into approved funding.
"Customers kept asking: 'When can get this?'"
I didn’t pitch the board — Janel did. The work I led made her pitch possible: research proving user need and market demand, CAB relationships validating design direction, Boardroom redesign demonstrating execution capability, in-depth scoping showing we’d thought through risks, and phased approach reducing uncertainty. The board approved funding in summer 2025, and team hiring began that fall — for the largest redesign in ResMan’s 20-year history.
The Takeaways
Don’t Wait for Perfect Conditions.
I didn’t ask for redesign funding in 2021. I built the evidence through research, demonstrated execution through Boardroom redesign and other initiatives, and delivered immediate value while preparing for the funding opportunity. When that opportunity emerged, four years of preparation made board approval possible.
Relationships catch what research can’t.
Multi-year Customer Advisory Board relationships revealed insights one-time research couldn’t capture. When internal teams wanted to remove features to simplify the platform, CAB feedback showed these features were critical to workflows. Long-term partnerships aren’t just about gathering feedback — they catch mistakes before you make them.
Ideas don’t get funded. Plans do.
Executives approve investments when they trust you’ve anticipated risks and planned realistically. In-depth scoping — risk analysis, honest engineering assessment, realistic timelines, phased approach — showed we’d thought through what could go wrong. The question isn’t “Is this a good idea?” but “Can this team actually execute it?”
Scope for reality, not approval.
Our CEO asked me to scope the redesign. I advocated for deeper analysis, insisted on realistic timelines, and recommended phased funding over one big ask. Scoping for approval gets you a yes. Scoping for reality gets you a yes that actually works.
The Multi-Year Strategy work proved what I bring to every initiative: build the foundation before you need it, deliver when opportunity arrives.