Go To Masters Show

Roxanne Dable is the Director of Sales Operations at Zendesk, where she focuses on driving operational excellence and aligning sales processes to deliver customer value at scale. On this episode of the Go To Masters Show, she shares insights from 15 years across banking, fintech, SaaS, and healthcare, including her experience as a fractional COO during the pandemic.

• Why the biggest CRM mistake is treating it as data storage instead of an enabler that helps teams work smarter
• How 100 required fields to close a deal forced reps to keep deals in spreadsheets, making pipeline reports unreliable
• The COO lens: quota decisions don't just affect sales but impact finance, recruiting, and customer success capacity

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Selling on Amazon as a brand is two completely different jobs depending on whether you’re 3P or 1P. In 3P, the brand controls price and carries inventory risk. In 1P, the retailer owns the inventory, controls price, and the brand has to think in terms of margin, not revenue. Most brands miss that shift, and the P&L tells the story.

Makarand Bidikar, Director of Revenue Recovery at SPS Commerce, has spent his career across finance, operations, and strategy at JP Morgan, Amazon, and most recently Carbon 6, the e-commerce growth-tech platform he ran as GM for 1P revenue recovery before SPS acquired it last year.

In this episode of GoToMasters, Makarand breaks down where 1P brands actually lose money, and it’s rarely where finance is looking. He gets into the ROI mindset that separates brands that triple their 1P sales in a year from ones that flatline; the 120-day cash cycle that quietly breaks brands long before their products fail; and what he calls death by a thousand paper cuts: deductions, compliance fees, and shortages that look small per transaction but aggregate to 5–10 percent of sales every year.

He’s equally direct on what separates companies that scale efficiently from ones that struggle. They codify revenue before they grow, defining pricing bands, ideal customer, and what counts as a good deal so growth doesn’t just add bad business to the P&L. They keep decision-making lean enough that nothing sits in no-man’s land. And they practice what Makarand calls discipline business paranoia: not fear, but the constant question of what breaks if we double, plateau, or lose 20 percent of margin.

If you’re a finance, RevOps, or e-commerce leader thinking about scaling discipline, profitability leakage, or how AI changes the operator’s job, this one’s worth your time.

Most RevOps job descriptions read like a contradiction. Strategic advisor. Tactical executor. Data analyst. Project manager. All at once.

Katrin Gurvich, GTM Business Partner at Navan, has a better frame for it: the role requires you to be bilingual. Not in the language sense, in the ability to switch context, altitude, and audience without losing the thread. One minute you're in a QBR presenting business risk to the CRO. The next you're debugging a Salesforce issue with a rep. Same day. Same person.

In this episode, Katrin breaks down what that actually looks like in practice, the four signals she uses to diagnose business health, why quota attainment can mask serious rep participation risk, how she thinks about pipeline coverage beyond the month-end snapshot, and what good CPQ does for trust across the whole revenue org.

She also gets into where AI genuinely earns its keep (thought partner, not magic), and what she'd tell anyone trying to break into this world: take the sales role if it's open, go to the events, and don't be precious about the path.

If you've ever struggled to explain what RevOps actually does or you're trying to get better at operating across every altitude of the business, this one's worth your time.

Matt Jacobson has spent 30 years in finance, investment banking, corporate strategy, venture investing, and the last 12 building and scaling venture-backed companies as CFO and COO. He's developed a simple framework for how careers and organizations grow: learning, doing, building. And in his telling, none of those phases ever fully ends.

In this episode of GoToMasters Finance Fireside, Matt breaks down what it actually means to build sustainable finance operations at a high-growth SaaS company, getting org structure right before anything else, assigning real ownership rather than tasks, and compounding small improvements week over week until the gap between where you started and where you are becomes undeniable.

He's equally direct on AI. Not hype, not magic, treat it like a junior analyst. It needs good prompts, constant correction, and a human who knows when the output is wrong. But when it works, it buys back the 15 and 30-minute chunks of time that add up to hours of strategic thinking you couldn't access before.

He also gets into comp plan design from a CFO's lens: why the instinct to set a 10% commission rate without checking the math against ACV and deal cycle is how you set reps up to fail and what RevOps actually needs to do to connect sales, finance, and operations without creating friction.

If you work in finance, RevOps, or GTM leadership at a growth-stage company, this one pays off.

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

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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

Connect with Jason: LinkedIn
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