The business grew past what
the system was built for.
Install the discipline. Establish visibility. Raise the performance ceiling. Scaling pressure resolves into predictable outcomes. The pattern repeats.
The symptoms look different depending on the situation.
Velocity slows without a clear cause. An acquisition closes and the integration never quite lands. Sales and product are running separate plays. The burn rate is moving in the wrong direction.
The situations differ. The gap is the same.
When the operating gap closes.
The metrics that matter start moving. The board conversation shifts from status to strategy. Competing roadmaps collapse into a single priority list. Performance becomes visible and predictable.
The pattern repeats.
The work falls into five domains.
Operating Discipline
One priority list. Alignment leads to acceleration. Cadence that makes performance visible.
Organizational Design
Structure that manifests the strategy. Set ownership where the work actually lands, with the talent to deliver.
Modernization
Decisions anchored to business outcomes, not technical preference. Most challenges are solved problems. The platform evolves under load, in production.
AI as Operating Leverage
Push the limits with control. Embedded in the product and the operating model. Value sequencing over novelty. Measurable rollouts.
Diligence Readiness
A process surfaces the gaps. Your diligence should expose them. Your operating model should constantly correct them — always ready for a process.
When the operating gap has become a board-level concern.
T2SA works with growth-stage and scaling SaaS companies. Typical situations include:
- Growth that has outpaced the operating system or stalled
- A post-acquisition integration that hasn't closed
- A GTM-to-product misalignment costing revenue
- A profitability mandate requiring structural change without breaking the business
Engagements are selective.
One engagement at a time.
Embedded, full-time, equity-aligned. Twenty-five years building and transforming growth-stage SaaS organizations, always under PE or VC discipline — multiple $100M+ P&L mandates across that span.
Engineer before executive — Draper Fellow and emerging technology engineer, then equity research covering software before two decades operating. That path produces a specific capability: the ability to read a business at the financial level, translate it into operating decisions, and move fast without losing the board.
Three mandates define the pattern. Entrust, Calabrio, Total Expert — PE- and VC-backed. Each time, the business had outgrown its operating system. Each time, the fix followed the same sequence.
Calabrio
Resolved critical product performance and reliability issues (>99.95% availability); doubled team productivity; ARR roughly doubled; SaaS mix transformed from ~20% to ~90%; unicorn exit.
Total Expert
First AI offering shipped and reached significant ARR in 9 months; new products reached 30% of ARR; R&D cost reduced >30% with throughput increasing >30%; returned business to profitable growth against severe industry headwinds.
Entrust — Business Unit Operations
Reversed multi-year declines across two business units — identity products to 13% annual growth, Government to 12% CAGR within three years — with expanded margins.
Entrust — Strategic
Partnered with CEO to reorient the company from sales/engineering-led to strategic/product-led. Redesigned portfolio mix. Secured board support for strategic direction, rebranding, and the broader transformation. Drove acquisition execution.
USAF Academy. Draper Fellow. National Security Agency. Piper Sandler. Roth Capital.