Case Studies

My track record.

Five operating roles and two successful exits, with the metrics to show for them. Every outcome here came from a full-time seat — CCO, COO, or VP — actually running the organization.

Sharpen CX · PE-backed (Teleo)
Role: Chief Customer Officer / Chief Operating Officer
Company: Sharpen CX — AI CCaaS platform, $14M → $25M ARR
Tenure: July 2023 – August 2025
70→100%
NDR
60→96%
GDR
30→10%
Churn

Restoring Retention Through a Three-Company Merger

Situation

I joined to work with a former CEO partner shortly after a PE firm acquired the company. Over the following months, the firm completed additional acquisitions to merge into the business, expanding the product footprint, building AI capability, and positioning the combined company for a sale in a few years.

Challenge

Integrating three businesses at once meant reconciling different account-management practices, product roadmaps, and customer bases under real time pressure, while the core platform needed stability work to reduce churn. NDR became the company's defining metric, the clearest signal of whether the merger was working.

Approach

  • Renewal, expansion, and upsell ownership moved from Sales into a newly built Customer Success function, built for sustained accountability instead of one-off wins.
  • Built and trained a new CSM install-base sales function from scratch, with playbooks covering renewals, expansion, and upsell, transitioning all accounts within one quarter.
  • Promoted from within to lead it rather than hiring externally (see "Liberate the Talent" on About).
  • Deployed AI workflows (ChatGPT, Claude, LinkedIn Sales Navigator) across a team of 4 to analyze customer health signals, product engagement, and ticket trends at scale, giving the team the ability to intervene proactively across 300+ accounts.
  • Pushed renewal rate increases averaging 5.2% against a 2% target.

Results

  • NDR: 70% → 100% | GDR: 60% → 96% | Churn: 30% → 10%
  • Achieved Rule of 20 in 2025, up from a $4M shortfall and 30% churn in 2023.
  • Time-to-value: reduced from 6 months to 2.5 months, with some implementations reaching as low as 5 weeks.

Lessons Learned

Integrating three businesses on an aggressive timeline taught me how much sequencing matters. In hindsight, I'd push earlier and harder for a pace the business could actually sustain, instead of absorbing pressure to move faster than the fundamentals allowed.

Torii · Series B (Tiger Global)
Chief Customer Officer · 2022 – 2023
SaaS Management Platform
25%+/mo
Account Expansion
New
Revenue Line Launched
↑↑
Forecast Accuracy

Built the expansion engine on top of a Series B raise.

I joined right after the round closed to build customer success and revenue expansion from scratch. Within six months, monthly account expansion was running above 25%. From there, I architected the predictive revenue visibility systems that gave leadership real forecast accuracy and led the pricing framework behind platform modularization. I also launched Contract Data Entry Services as a new revenue line.

Hyperscience · Series B/C (Bessemer)
Role: Chief Customer Officer
Company: Hyperscience — AI Document Automation, $8M → $30M ARR
Tenure: January 2020 – February 2022
6 → 70
CS Team Built
110%
NDR Maintained
$30M
ARR Protected

Scaling Customer Success Through Hypergrowth

Situation

I joined to build Hyperscience's Customer Success organization from the ground up during a period of rapid international scaling, as the company grew its customer base from 16 to 120 and expanded well beyond its US footprint.

Challenge

Sustaining retention while scaling a global organization at speed is a different problem than fixing one. The team needed to grow from 6 people to dozens, across 9 countries, without losing the consistency, accountability, or customer outcomes that had supported the business at a smaller scale, all while protecting a fast-growing $30M ARR base.

Approach

  • Built the global CS organization from 6 to 70 people across 9 countries in two years, including hiring and leading Directors and VPs by region.
  • Drove customer adoption of the platform's AI/ML automation capabilities, accelerating time-to-value by 50%.
  • Created marketecture diagrams and contributed to RFP responses, translating platform architecture and business value for enterprise prospects and customers. One example: the Veterans Administration, where the platform helped accelerate insurance claims processing by 60%.
  • Launched an Academy and Partner Marketplace, enabling ecosystem growth with partners including IBM, Accenture, Deloitte, and McKinsey.

Results

  • NDR: sustained at 110% throughout the highest-growth period.
  • Team: scaled from 6 to 70 across 9 countries in two years.
  • Customer base: grew from 16 to 120 accounts.
  • $30M ARR protected through the scaling period, with measurable customer outcomes (60% faster claims processing for a major government customer).

Lessons Learned

Scaling a CS organization this fast only works if regional leadership is empowered early. Trying to manage 9 countries directly, instead of through strong Directors and VPs, would have capped how fast we could responsibly grow. Investing in partner enablement (Academy, Marketplace) early paid off later, extending the team's reach without proportional headcount.

JK Group → CyberGrants · Acquired
Role: Vice President, Professional Services
Company: JK Group (acquired by CyberGrants) — Corporate Philanthropy SaaS
Tenure: November 2012 – June 2018
+160%
Implementation Throughput
3x
Services Revenue
60→93%
Call Center Answer Rate

Modernizing Customer Success to Drive an Acquisition

Situation

I joined JK Group to lead a turnaround across all Customer Success functions: Professional Services, Customer Success Management, Support, and Technical Services, working again with a former CEO partner. The board had brought him in to take a company running on aging technology and operating practices and position it for sale, which meant modernizing operations to a contemporary standard and launching a new product on a modern tech stack.

Challenge

Turning around four functions at once, while a new platform was being built in parallel, meant the operating model had to hold up under a real product transition, not just read well in a board deck. Whatever we built needed to support both the legacy product, still generating revenue, and the new platform once it shipped.

Approach

  • Rebuilt implementation methodology and delivery practices across Professional Services, cutting time-to-value and making outcomes repeatable instead of dependent on individual heroics.
  • Applied the same operating discipline built at SumTotal/CyberShift, including standardized methodology, workflow, and SOW practices, to a company starting from a much further-behind baseline.
  • Led the team through the launch of a new platform on a modern tech stack, reaching its first customer implementation.
  • Within two years, turned around all four CS functions, with shorter, more sustainable delivery cycles across the board.

Results

  • Within two years, the board moved the company to a sale, leading to acquisition by CyberGrants.
  • Retained post-acquisition and asked to take on CyberGrants' own CS functions as well, ending up responsible for Professional Services, Customer Success, and Support across two product lines, leading a 55-person organization including Regional Directors and positioning the company for its next investor exit.
  • Increased implementation throughput 160% and grew services revenue 3x over the full tenure.
  • Orchestrated 200+ legacy client migrations, reducing cycle time 60%.
  • Drove call center answer rates from 60% to 93%.

Lessons Learned

The operating discipline that worked at SumTotal/CyberShift transferred directly here. The real test was making it hold up through a live product transition. Modernizing delivery while a brand-new platform was being built and launched in parallel taught me that sequencing the turnaround and the launch correctly mattered as much as executing either one well individually.

CyberShift → SumTotal Systems · PE-backed (Vista Equity)
Roles: Project Manager → Implementation Consultant → Practice Director → Solution Consultant → Director of Solution Consulting → VP, Channel Services → VP, Professional & Channel Services
Company: CyberShift (acquired by SumTotal Systems) — Enterprise WFM & HCM SaaS, $4M → $200M ARR
Tenure: July 1998 – October 2012
$4M→$200M
ARR Growth
−113→+23%
GM Turnaround
25→60%
Partner Win Rate

From Employee #13 to Global VP: Building a Function Through Every Stage of Growth

The Arc

I joined CyberShift as employee #13, as a Project Manager, when the company was still finding its footing. Over the next several years, I moved through nearly every customer-facing function the company had, each time taking on whatever problem needed solving next instead of following a planned track:

  • Top Implementation Consultant — ran the most and fastest implementations in the company for several years.
  • Practice Director — promoted to run a combined team of project managers, implementation consultants, trainers, and technical consultants. Built the company's first formal implementation methodology, workflow standards, and SOW templates. Delivery had been ad hoc before that; this made it repeatable at scale.
  • Solution Consultant — moved to pre-sales as the technical trusted advisor, scoping projects and constructing SOWs ahead of the sale.
  • Director of Solution Consulting — promoted to run the function. Pulled several of the best people from the implementation and technical consulting teams into Solution Consulting; many became the company's top SCs for years, even after I left (an early version of "Liberate the Talent," see About).

The Channel Problem

CyberShift's growth strategy shifted toward channel partners, each new partnership expected to contribute $1M in year two. Post-agreement partner support (sales-cycle support, implementation, post-launch) was running at a triple-digit negative gross margin.

  • VP of Channel Services — promoted to take over the channel support model and fix the unit economics.
  • Rebuilt the channel support model, improving gross margin from -113% to +23% within 1.5 years.
  • Built a white-label partnership generating $10M+ in ARR and 500+ new accounts.
  • Increased partner win rates from 25% to 60% through enablement programs.

The Acquisition

CyberShift's turnaround and channel results contributed to its acquisition by SumTotal Systems, which wanted to add Workforce Management and Expense Management to its portfolio. I was asked to stay on as one of four global VPs of Professional Services, where I:

  • Led a 60-person global organization, including Regional Directors across US, Canada, EMEA, and APAC.
  • Managed 332 implementations globally, including deep technical engagement with customer IT executives on architecture, security, and hosting.
  • Managed major public-sector relationships, including NYC Department of Education ($25M), City of Chicago, City of Las Vegas, and Cook County, IL.

Results

  • Company growth: $4M → $200M ARR (750%) from CyberShift's early days through the SumTotal era, leading to a successful exit (Vista Equity Partners).
  • Gross margin: -113% → +23% in 1.5 years.
  • Channel ARR: $10M+ generated, 500+ new accounts.
  • Partner win rates: 25% → 60%.

Lessons Learned

The clearest pattern across 14 years here: every promotion came from solving the next visible problem, never from a planned path. That only works if you're willing to actually own the foundational parts first, methodology, SOW standards, partner enablement mechanics, before the bigger title shows up. The channel turnaround reinforced something I carried into every later role: partner win-rate enablement has to come before partner volume, or you scale a losing unit economics problem faster.