Courtney Hickey is the Director of Revenue Operations at ParentSquare, a K12 communication platform serving school districts across the US. She didn't come up through traditional RevOps channels — she started in administrative and legal roles, learned the business by sitting in on executive conversations, and built her way into operations from the ground up. On this episode of the Go To Masters Show, she shares what that unconventional path taught her about designing systems that flex, where comp plans break trust before anyone notices, and why she thinks AI's biggest promise has nothing to do with speed.

• Why rigidity is the biggest risk in RevOps and why falling in love with the problem beats falling in love with the process
• The quiet side of comp trust erosion: when the RevOps team can't explain the plan either, you've already lost on both ends
• Why AI's real value isn't speed but signal quality, and what it looks like when teams build for the wrong metric

Evgenia Vereshchak is the Director of Revenue Operations at Procurify, a spend management platform built for mid-market companies, based in Vancouver. She spent eight years at the company, starting as a BDR before moving into RevOps. On this episode of the Go To Masters Show, she shares what building a RevOps function from scratch actually requires, why process has to come before tools, and what most teams get wrong about comp planning before they ever run the numbers.

• Why RevOps should never sit under sales, and what happens to long-term revenue health when it does
• The right order for building RevOps from scratch: ICP clarity and customer lifecycle first, team accountability second, tech stack last
• Why every comp plan is a behavioral experiment, and why modeling at 50%, 80%, and 100% attainment before rollout is non-negotiable

Jatinder Dohil is the Global Head of Revenue Operations at ThetaRay, where they build AI-powered tools to help financial institutions detect money laundering and human trafficking. Before ThetaRay, he spent 20 years in revenue operations across organizations ranging from 10,000+ employees to early-stage startups.

In this episode, Jatinder breaks down his five-pillar RevOps framework: data and insights, systems, process, commissions planning, and customer 360. He explains why forecasting accuracy within a 5% threshold changes how the entire business plans, shares a salary analogy that makes unpredictable revenue feel personal, and talks about how AI tools like Copilot are changing what sales reps can focus on during live conversations.

He also gets specific on commission planning and CPQ: why simplicity matters more than sophistication, what good CRM hygiene actually requires, and the three things he’d tell anyone building a RevOps function from scratch.

Topics covered: RevOps frameworks, forecasting and predictability, commission planning, CPQ implementation, AI in revenue operations, CRM structure, and building RevOps teams across company sizes.

Samantha Joswick is the Senior Manager of Sales Operations at H2O.ai, where she owns the full GTM engine: compensation, deal desk, analytics, and systems. Before H2O.ai, she spent several years at Adobe working on product-level comp plans for the global digital marketing sales organization, and led end-to-end compensation at Intermedia Cloud Communications.

In this episode, Samantha talks about how she fell into sales ops by accident, spotted a quota overlap at Adobe that leadership was dismissing as rep complaints, and used data to prove it was structural. She shares her framework for comp design: start with the math, but don’t worship it. Use quantitative models as guardrails, then layer on qualitative context from the field to figure out what’s actually sustainable.

She also covers how owning deal desk changed the way she thinks about incentives across the full deal lifecycle, where AI adds real value in sales ops (and where human judgment still has to stay in the loop), and her three pieces of advice for anyone building a career in the space: get close to the field, respect the data without worshiping it, and think in systems.

Andre Serpa is the Area Vice President for Latin America at ClickHouse, a real-time analytical database company, based in São Paulo. He spent a decade at Microsoft, nearly six years as one of the earliest employees of what became Google Cloud, and then four years each at Elastic and Neo4j, always building LATAM go-to-market operations from the ground up. On this episode of the Go To Masters Show, he shares what two decades of market-building in Latin America actually taught him about partnerships, talent gaps, local nuance, and why the companies that get the region right go partner-first before anything else.

• Why partner-first isn't optional in LATAM, and the billing, collections, compliance, and talent realities that make going direct alone a costly mistake
• The three lessons from Microsoft and Google he still runs GTM by today: data-driven decisions, measurable goals at every level, and the discipline of execution cadence
• How AI is changing sales operations from the inside, and the real-time backend performance bottleneck that most operators never think about

Connect with Andre: LinkedIn
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Jason Martin is the VP of Credit and Collections at Kaseya, a global IT management software company operating across North America, EMEA, and APAC. He spent 21 years at Datavant, rising from entry-level collector to Head of Finance Operations and watching the industry move from paper records to bot automation to AI. On this episode of the Go To Masters Show Finance Fireside, he shares what finance transformation actually looks like from the inside: why culture is the real barrier to AI adoption, and what it takes to lead global teams through that kind of change.

• Why 80% of finance use cases are automatable today, and what the companies sitting on the sidelines will face in five years
• The three-part leadership framework Jason learned from a mentor (command, calm, and candor), and why candor sometimes means walking away from revenue
• How he unified distributed teams across three geographies by fixing the one thing most global leaders overlook: inclusion in the same room at the same time

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Matt Dornfeld is the Senior Director of Global AI GTM at Commerce, the public holding company behind BigCommerce and Feedonomics, where he leads the effort to embed AI across every workflow in the revenue organization. On this episode of the Go To Masters Show, he shares what building an AI GTM practice from the inside actually looks like. He covers why most teams sabotage themselves before they start, and what separates companies getting real outcomes from those chasing shiny objects.

• Why doing one AI use case completely beats running 50 halfway, and the FOMO that keeps pushing teams toward the latter
• The data-first framework: take stock of what you have, centralize it, connect the sets, and only then ask what becomes possible
• How top brands decide whether a new channel is worth the investment, and why focus is a competitive advantage most teams underestimate

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Shiv Walia is the Director of Sales Compensation at A Place For Mom, leading comp strategy in the senior living industry. On this episode of the Go To Masters Show, he shares insights from 12 years in GTM, starting as a computer engineer at Accenture, then moving through sales ops at Dell and Mindbody before specializing in compensation across B2B and B2C models.

• Why a bad comp plan causes attrition faster than anything—and why what reps focus on is always what they get paid on
• How showing a graph of rep productivity going from 20 to 40 sales overnight made leadership realize you can't 2X productivity instantly
• Why sales comp is an emotional topic about someone's livelihood—data alone won't get buy-in if you ignore the human side

Connect with Shiv: LinkedIn

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