Robby Halford (Momentive Software) on Why Enablement Needs the CRO, Ramp Design & AI Coaching

Robby Halford (Momentive Software) on Why Enablement Needs the CRO, Ramp Design & AI Coaching

Most ramp programs are just bad instructional design dressed up as onboarding. A week of PowerPoints, a parade of decks, and then we throw new sellers on the floor and hope. Robby Halford has watched this break sales teams for over a decade — and built something different. Robby is VP of Go-to-Market Performance at Momentive Software, where he oversees enablement, business development, marketing operations, and sales operations. He started his career as a middle school English teacher, spent six years carrying a bag (and made President's Club in his first full year), and is finishing a doctorate in curriculum and instruction. He brings the seriousness of an academic and the empathy of a former seller to every program he builds. He joins GoToMasters to argue that enablement is not a slide-making team. It's the execution wing of every strategic decision a leadership team makes, and the function only works when it has a direct seat at the CRO's table. He breaks down why he pays new sellers to learn for a full month before they touch a quota, why CSMs are the most under-enabled team in most orgs, why throwing more enablement at a problem rarely fixes it, and why AI feedback often lands better than manager feedback — because it has no feelings to hurt. If you're building an enablement function, designing a ramp program, or trying to elevate learning into a revenue-generating activity, this one's worth your time.

Hadas Sheinfeld (Sisense) on Leading the Energy, Hiring for Grit & Acting Like a Director First

The biggest mistake finance teams make today is hiring for patterns. Same degree, same Big Four background, same SaaS experience — and then leadership wonders why they get average results. Hadas Sheinfeld has spent her career making the opposite bet. Hadas is Director of Finance at Sisense, where she manages finance operations across Israel, the US, and Ukraine. She joins GoToMasters for a conversation about what it actually takes to build a finance team that compounds value over time — and what it took for her to act like a director before anyone formally promoted her into the role. She breaks down the three pillars she uses to hire her team: grit over templates, ability over titles, and pushing finance from data checkers into storytellers who can tell leadership what the numbers mean for the company's future. She gets into the moment that turned her from a temporary fix into a real leader (a team member asked her what events she was planning that year), and the dangerous blind spot most managers carry — assuming their employees don't have the courage to move on, when the best ones already know they do. If you're hiring into a finance function, building a team you want to keep, or trying to break out of a role you've outgrown without waiting for a formal promotion, this one's worth your time.

Caroline Rocha (Just Eat Takeaway) on Designing Comp Across Cultures, AI Myths & Comp Transparency

A 30% productivity gain from AI delivered zero more customer visits. Caroline Rocha knows a comp team that lived through that exact outcome — the hours just moved to weekends and evenings, where the sellers had quietly been working all along. Caroline is Manager of Global Services Compensation at Just Eat Takeaway, with 15+ years designing sales incentives across Brazil, Japan, and the Netherlands. She joins GoToMasters to unpack what international comp design actually looks like, and where most companies misread both culture and AI. She gets into the cultural calibration behind global comp plans, why comp can never become a black box reps can't see into, and why teams should base decisions on evidence of what AI actually does — not what it should do. If you're designing comp across markets or figuring out where AI fits in the comp function, this one's worth your time.

Why the Person Running Your Comp Plan Should Be the One Closest to the Pipeline

Daniel Wolman is Head of Incentive Compensation at Dext, the bookkeeping automation platform, where he runs comp solo across multiple regions after 15 years in ops and RevOps. In this episode, he makes the case that RevOps should own comp because they're the only function that designs for behavior rather than cost control or fairness. He walks through how Dext restructured their account management plans from a single net revenue metric to split growth and retention targets, how to spot when reps are sandbagging deals because the plan is broken, and why CSM comp is so hard to get right when the role doesn't hold a revenue number. He also covers performance management, the shelf life of salespeople, and how to run a global comp function as a one-person team.

If a Rep Switches Products Because of Comp, Your Plan Is Working Against You

Ajay Erogbogbo is VP and Head of Revenue Operations and Strategic Initiatives at Pathward, a publicly listed financial holding company, where he designs incentive comp for commercial lending officers. In this episode, he breaks down how variable comp works when it's tied to loan origination volume with two-year clawback windows, why standardizing comp across product lines creates distortion when the risk profiles are different, and how he distinguishes between a performance issue and a design issue during monthly reviews. He also covers why the biggest structural comp mistake is designing for what's easy to measure rather than what creates value, and how giving BDOs a simulator to model their earnings changes the entire plan rollout conversation.