The metric that got Taylor Thomson promoted tells a straightforward story: average annual contract values at WITHIN jumped from $250,000 to $1.8 million between March 2021 and March 2023. That’s 620% growth in 24 months.
But the story behind that number is anything but straightforward.
Thomson didn’t raise prices. He didn’t land one massive account that skewed the average. He rebuilt the machinery that connects marketing spending to client acquisition to revenue recognition—transforming WITHIN from a mid-market agency into a player competing for Fortune 500 relationships.
“We successfully transitioned the business model from transactional to enterprise,” Thomson explains. The shift required changing everything: who WITHIN targeted, how they positioned services, what promises they made, and how they delivered value.
The Conversion Rate That Mattered
While the 620% contract value increase captured attention, Thomson points to a different number as proof the transformation worked: trial-to-term conversion rates improved 33 percentage points.
Before Thomson redesigned the onboarding process, roughly two-thirds of clients who started working with WITHIN eventually signed long-term contracts. After the redesign, that figure climbed to over 95%. The difference translated to $7.6 million in incremental annual revenue.
“We revamped the new-client onboarding process, resulting in a remarkable 33 percentage point increase in trial-to-term conversion rate, equating to $7.6mm in incremental revenue year-over-year,” Thomson notes.
What changed? Thomson systematized every touchpoint during the first 90 days of a client relationship.
New clients now receive a detailed roadmap showing exactly what will happen each week. Account managers follow scripts ensuring critical conversations happen at the right moments. Regular check-ins identify problems before they become deal-breakers. Success metrics get defined collaboratively rather than assumed unilaterally.
The process might sound basic, but most agencies wing it. They assign an account manager, schedule a kickoff call, and hope things work out. When clients don’t renew, they blame “bad fit” or “unrealistic expectations” rather than examining their own systems.
Thomson’s background in revenue operations gave him a different lens. He could see where handoffs failed, where communication broke down, where clients lost confidence. Each failure point became an opportunity for process improvement.
The Dashboard That Aligned Everything
Before Thomson joined WITHIN in March 2021, the company lacked a unified view of its revenue engine. Marketing tracked lead generation. Sales tracked deal closure. Client success tracked retention. Finance tracked bookings and collections. But nobody connected these data streams to understand cause and effect.
Thomson built WITHIN’s first comprehensive revenue model and dashboard. The tool tracked not just departmental metrics but how they related. How many marketing-qualified leads became sales-qualified leads? Which lead sources produced customers who renewed? What was the average time from first contact to signed contract? How did win rates vary by industry, company size, or initial service purchased?
“We developed the company’s first-ever comprehensive revenue model and dashboard, providing invaluable insights to executive leadership and supporting overall business strategy,” Thomson explains.
The dashboard revealed uncomfortable truths. Some marketing campaigns generated impressive lead volumes but terrible conversion rates because they attracted companies too small to afford WITHIN’s services. Some sales tactics closed deals quickly but produced clients who churned within months because expectations weren’t aligned.
Armed with data, Thomson could make changes that actually moved numbers. Marketing shifted budget toward campaigns that attracted qualified prospects rather than maximum traffic. Sales adjusted qualification criteria to filter out companies unlikely to succeed. Client success implemented early warning systems to identify at-risk accounts before they canceled.
The compound effect of these adjustments drove the 620% increase in contract values and the 33-point improvement in conversion rates.
The Service Level Agreements Nobody Wanted
Thomson’s next move seemed bureaucratic: he implemented Service Level Agreements across departments. Marketing committed to delivering specific quantities and qualities of leads. Business development committed to follow-up timeframes. Sales committed to handoff protocols. Client success committed to response windows.
“We implemented a series of department-wide Service Level Agreements (SLAs), fostering collaboration and communication among teams to drive efficiency and alignment,” Thomson notes.
Teams initially resisted. SLAs felt like micromanagement, like surveillance, like another layer of corporate process getting in the way of doing actual work. But Thomson framed them differently: as coordination mechanisms rather than control mechanisms.
The SLAs made visible what was previously invisible. If marketing delivered 100 leads but only 15 became opportunities, the data clarified whether the problem was lead quality or follow-up discipline. If sales closed 30 deals but only 20 onboarded successfully, the breakdown revealed whether qualification criteria were wrong or handoff processes were broken.
Over time, teams came to rely on the SLAs. They provided objective grounds for requesting resources (“We’re hitting our lead targets but conversion is suffering because we’re understaffed”) or pushing back on unreasonable expectations (“You asked us to double output but didn’t increase budget or headcount”).
The SLAs also enabled better forecasting. Rather than treating revenue as unpredictable, Thomson could model how changes in one part of the system would flow through to outcomes. If marketing increased lead generation by 20%, he could predict with reasonable accuracy how many additional deals would close three months later.
The AI Integration That Worked
While many companies experiment with AI tools without clear use cases, Thomson led cross-functional projects with data science and IT teams to build internal databases using GPT-4 and Bard.
The applications were specific rather than speculative. WITHIN needed better systems for capturing institutional knowledge—lessons learned from past campaigns, client preferences, competitive intelligence, industry trends. That information existed in email threads, Slack conversations, meeting notes, and people’s heads. But accessing it required knowing who to ask or where to look.
Thomson’s team built databases that could surface relevant information on demand. Account managers preparing for client calls could query what similar clients had requested. Strategists developing campaign proposals could review what worked for comparable brands. Sales teams researching prospects could find connections between those companies and existing clients.
“We lead cross-functional projects with data science and IT teams to develop internal databases using state-of-the-art generative AI technologies like GPT-4 and Bard,” Thomson explains.
The tools didn’t replace human judgment. They augmented it by making collective knowledge accessible rather than trapped in silos.
The Survey Secret
Thomson also spearheads WITHIN’s client satisfaction survey program, which consistently achieves over 50% quarterly response rates—roughly triple the industry average for B2B service providers.
The secret isn’t survey design or incentive structure. It’s what happens after clients respond.
Most companies send satisfaction surveys, collect responses, and file them away. Maybe someone reads them. Maybe leadership sees a summary. But individual responses rarely trigger action.
Thomson built systems to route feedback to responsible parties within 24 hours. If a client expressed frustration with communication frequency, their account manager received that feedback immediately. If someone praised a specific deliverable, the team who created it heard about it that day. If multiple clients mentioned the same issue, leadership reviewed it at the next executive meeting.
“We spearhead robust client satisfaction survey initiatives, achieving an average response rate of over 50% quarterly; designed company-wide dashboards for comprehensive analysis and reporting of survey results,” Thomson notes.
Clients noticed that providing feedback led to changes. Account managers followed up on concerns raised in surveys. Services improved based on suggestions. Problems got fixed rather than ignored. That responsiveness encouraged continued participation.
The survey data also fed back into business operations. If clients consistently mentioned unclear pricing, sales teams adjusted how they presented proposals. If onboarding felt rushed, client success extended timelines. If certain services underdelivered, product teams prioritized improvements.
The 50% response rate wasn’t the goal. The goal was creating feedback loops that continuously improved service delivery. The response rate was merely evidence those loops worked.
The Morning Routine That Drives Everything
Thomson’s daily routine provides insight into how he thinks about his role. Each morning, before meetings begin, he spends 15-20 minutes reading industry newsletters—Modern Retail, Glossy, Morning Brew, and sector-specific publications.
He’s not reading for personal edification. He’s hunting for signals relevant to WITHIN’s clients and prospects: news about funding rounds, reports on consumer behavior shifts, announcements about executive changes, analysis of market dynamics.
Then he curates a Google sheet of the most relevant articles and shares it with his team. Business development uses it to personalize outreach. Account managers use it to anticipate client concerns. Strategy teams use it to identify emerging opportunities.
“I probably read 15 different morning newsletters, and then I do this for my team actually,” Thomson explains. “I take those newsletters. I find the most interesting or the most relevant articles, and I put them into a Google sheet.”
The practice embodies Thomson’s philosophy about finance leadership: the role isn’t just managing budgets and forecasting revenue. It’s synthesizing information across domains to help the organization make better decisions.
The MBA That Happened Simultaneously
Throughout all this operational work—rebuilding onboarding processes, implementing SLAs, developing revenue dashboards, integrating AI tools—Thomson was pursuing an MBA from the University of Virginia’s Darden School of Business.
He enrolled in 2022 and graduated in May 2024, finishing in the top 15% of his class while working full-time. The dual commitment reflected his conviction that business fundamentals matter even as technology transforms how work gets done.
The MBA curriculum covered finance, data analytics, and strategy—topics directly applicable to Thomson’s role. But the program also forced him to step back from tactical execution and think about broader strategic questions: What business models work in different industries? How do successful companies allocate capital? What distinguishes high-performing organizations?
“First Year Academic Achievement Award (Top 15% of Class),” his LinkedIn profile notes, marking the recognition he received.
The credential mattered less than the thinking it represented. Thomson could have stayed in his Director of Revenue Operations role indefinitely. He was good at it. The company valued him. But he wanted to develop expertise in areas beyond operations: financial forecasting, capital allocation, strategic planning.
The Promotions That Validated the Approach
Thomson was promoted to Head of Revenue Strategy and Operations in January 2024, then to Head of Finance in June 2024. The rapid progression reflected WITHIN’s recognition that his skills were relevant beyond revenue operations.
As Head of Finance, Thomson now manages company-wide P&L reporting and analytics, oversees accounting operations, develops forecasting strategies across business units, and orchestrates annual compensation planning. He also strategically manages the finance technology and tools budget, optimizing resource allocation for maximum impact on revenue generation.
“As the Head of Finance, I navigate financial forecasting, technology management, and strategic planning, fueling growth and operational excellence,” Thomson explains on his profile. “Embracing innovation, I continually refine our processes and tools to stay ahead in a dynamic business landscape.”
The role combines traditional finance responsibilities with the systems-thinking approach Thomson developed in revenue operations. He’s not just tracking numbers—he’s building the infrastructure that enables better decision-making across the organization.
His revenue operations team is expanding from three people to a larger group over the next several months. The growth will support work across enablement, technology, analytics, performance management, and operational workflows.
“We’re growing both teams, but revenue operations is a big focus of ours, and so we’re growing the revenue operations team pretty quickly over the next three to six months,” Thomson notes.
The Pattern Behind the Numbers
Look at the full arc of Thomson’s career and a pattern emerges. He spent three and a half years at Ridgetop Research developing the ability to quickly synthesize information across disparate industries. He moved through roles at Custora learning how customer data platforms work and don’t work. He joined WITHIN and rebuilt their revenue operations from the ground up.
Each experience built toward the same capability: seeing systems holistically and understanding how changes in one part affect outcomes elsewhere.
That capability explains the 620% increase in contract values. It wasn’t one brilliant insight or lucky break. It was systematic improvements across multiple processes that compounded over time. Better targeting produced better leads. Better qualification produced better customers. Better onboarding produced better retention. Better retention enabled higher pricing and expanded services.
Thomson’s approach suggests that the future of finance leadership may look different than its past. CFOs need to understand revenue mechanics deeply, know how business development actually works, and connect financial planning to customer behavior rather than treating it as an abstract exercise.
Whether that model can scale beyond agencies to larger enterprises remains untested. But for companies willing to invest in building systems rather than chasing quick wins, Thomson offers a proven playbook: create visibility across functions, align incentives with actual outcomes, measure what matters rather than what’s easy, and continuously refine processes based on data.
The numbers don’t lie. 620% growth in contract values. 33 percentage points improvement in conversion rates. $7.6 million in incremental revenue. 50% survey response rates. Top 15% MBA class ranking.
But the numbers also don’t tell the full story. Behind each metric is a decision to build differently, organize differently, and lead differently. Thomson’s success stems not from working harder or being smarter but from seeing connections that others miss and building systems that make those connections productive.
That might be the most important number of all: zero—as in the number of shortcuts taken, quick fixes attempted, or conventional wisdoms accepted without question. Thomson rebuilt the machinery piece by piece, and the results speak for themselves.
