YISRAEL KOPSTICK

Career Accomplishments

I'm a Customer Success leader who builds commercial growth engines. Over 13+ years in B2B SaaS, across PropTech, payments, and multi-product platforms, I've owned the full post-sale lifecycle and the commercial outcomes that come with it. I've built CS organizations from scratch, rebuilt reactive ones into proactive growth functions, and led teams through acquisitions, platform consolidations, and aggressive growth phases. The through-line of my career is simple: I take customer relationships and turn them into durable, predictable revenue.

The operating model for Customer Success is changing fast. I treat AI as core operating infrastructure, not a future bet, and I'm building my team to do the same. I've made it my business to lead that change rather than be caught by it.

Customer Success

When I took over Customer Success at Payquad, the function operated as reactive support, closing tickets, answering questions, and putting out fires. It wasn't built to drive commercial outcomes. I rebuilt it from the ground up. We introduced health scoring, customer segmentation, structured renewal forecasting, and lifecycle playbooks for every stage from onboarding through expansion. I personally took ownership of strategic and at-risk accounts while coaching the team on the day-to-day customer interactions that build trust over time. The function is now aligned to NRR and GRR, with renewal pipeline visibility and expansion motions running consistently across the customer base. We've maintained over 100% Net Revenue Retention and below 3% annual churn across a $10M+ portfolio.

At Rent Magic, my early years in enterprise account management taught me that retention is built, not maintained. I designed and executed structured save flows, onboarding redesigns, and proactive at-risk engagement programs that reduced churn by 50% across a portfolio of 100+ enterprise accounts. The same work also drove 300% expansion ARR growth, because the discipline that prevents churn is the same discipline that surfaces expansion. Customers who feel understood buy more.

Business Operations & Integration

At Alsoss, I led customer integration strategy across five acquisitions during a complex multi-brand platform consolidation. Integration work is brutal on customers. They get migrated, re-onboarded, and asked to relearn workflows they've already mastered. My team's job was to make that invisible. We built a structured customer journey for each integration, aligned systems and processes across legacy brands, and held retention while the platform was being rebuilt underneath us. The North American expansion initiatives we supported during this period delivered a 25% revenue uplift within 60 days.

At Payquad, I developed the Customer Success capacity model ahead of the largest client deployment in the company's history. Rather than wait for the deployment to expose understaffing, I modeled the workload, built the case for additional headcount, and coordinated cross-functional resources across Product, Support, and Finance to ensure delivery readiness. The deployment landed without service degradation, which is the highest compliment any operations leader can earn.

Driving Revenue

At StockUpMarket, I built and led a 15-person Customer Success and Revenue Operations organization that owned the full customer lifecycle. The challenge was scale. We needed every customer-facing person, not just the CSMs, to be commercially aware. I trained the entire team on identifying upsell and cross-sell opportunities tied to product adoption, restructured how we tracked customer engagement, and built integrated systems across CRM, ecommerce, and support workflows. The result was 90% MRR growth and 100% YoY wholesale expansion through structured multi-product adoption.

At Payquad, I oversee payment processing operations supporting more than 250,000 transactions and $370M+ in annual processed payments. The role isn't just about managing volume. It's about treating payment reliability as a commercial asset. SLA performance, processing accuracy, and platform uptime are part of the customer value proposition, and they directly affect retention and expansion conversations.

Building Teams & Culture

Across every role, I've built teams that outperform their size. At StockUpMarket I scaled the CS and RevOps function to 15 people. At Payquad I've built a player-coach culture where the team is held accountable to commercial outcomes but supported with the playbooks, tools, and coaching to deliver. I believe the best CS teams operate with three things in balance: clear ownership, real autonomy, and an honest leader who tells them the truth, kindly but clearly.

AI as an Operating Model

I use AI tools every day, for account analysis, drafting customer communications, prepping QBRs, synthesizing customer feedback at scale, and accelerating playbook iteration. This isn't a productivity gimmick. It materially changes the output a single CSM can produce and how much time my team can spend on the actual customer conversation. CS leaders who don't operationalize AI in the next 12 to 18 months will be at a structural disadvantage. I'm making sure my team isn't on that side of the line.

Net Revenue Retention (NRR) ownership, Gross Revenue Retention (GRR), Churn Reduction, Save Flow Design, Renewal Forecasting, Expansion Strategy, Upsell & Cross-Sell Motions, Multi-Product Adoption, Customer Health Scoring, Risk Identification & Mitigation, Lifecycle Playbook Design, Customer Segmentation, Voice of Customer Programs

Player-Coach Leadership, Hiring & Talent Development, Coaching Frameworks, Career Pathing, Performance Management, Cross-Functional Team Building, Distributed Team Management, Player-to-Manager Development

Post-Acquisition Integration, Multi-Brand Platform Consolidation, Capacity Planning, Process Standardization, Operational Playbooks, Cross-Functional Workflow Design, Pipeline Visibility, KPI Design & Reporting

Daily AI Practitioner (Claude, ChatGPT, automation tooling), AI-Assisted Account Analysis, AI-Driven Workflow Design, CRM Systems, Health Scoring Tools, Revenue Analytics

P&L Partnership, Pricing Strategy, Margin Optimization, Forecasting, Bookkeeping & Financial Statement Oversight, Vendor Negotiation, Budget Management

B2B SaaS, PropTech, Payments & Fintech, eCommerce, Vertical Market SaaS, Commercial Real Estate, Non-Profit Operations

I've done this twice. At Payquad and at StockUpMarket, I inherited Customer Success functions that were operating as support, not as commercial drivers, and I rebuilt them around retention, expansion, and accountability. The work isn't glamorous. It's structured playbooks, health scoring, renewal forecasting, hard conversations about ownership, and the discipline to hold the line until the new model takes hold. But the outcome is a function that drives durable revenue instead of reacting to last week's tickets.

Across every senior role I've held, the job has stretched well beyond a single function. At StockUpMarket I owned Sales, Customer Success, and Revenue Operations. At Alsoss I directed lifecycle, sales operations, and IT. At the Foundation I ran finance, legal coordination, marketing oversight, and technology development. Operating across functions taught me to build systems and hire people I trust, then get out of the way. It's also why I'm comfortable in ambiguity. Most senior roles aren't a clean job description.

At StockUpMarket I scaled a Customer Success and Revenue Operations team to 15 people. The mark of a good team isn't size, it's leverage. I look for people who are coachable, commercially aware, and honest about what they don't know yet. Then I hold them to a high standard and give them the tools and air cover to grow into it. Several people I've hired have gone on to build their own teams, and that's the metric I'm proudest of.

I use AI tools every day. To analyze accounts, draft customer communications, prep QBRs, synthesize feedback at scale, and accelerate playbook iteration. AI hasn't replaced any of the work, but it has materially changed how much my team can produce and where they spend their time. I'm building the operating model that the next generation of CS organizations will run on, and I want to be ahead of that curve, not behind it.

Customers don't buy features. They buy outcomes. The work I do best is sitting across from a senior stakeholder, understanding the business problem they're trying to solve, and translating our platform into the language of that problem. Renewal becomes obvious. Expansion becomes natural. Churn becomes rare. Everything else is mechanics.

I listen for two weeks before I touch anything. The fastest way to lose a team is to walk in with answers before you understand the problem. I sit in on customer calls, read tickets, look at health data, and ask every CSM the same three questions. What are you proudest of, what's broken, and what would you change tomorrow if you could. By week three I've usually got 80% of the diagnosis. Then we build..

It looks like the customer doesn't realize they're being managed. They just feel like someone gets their business. The best CS work is invisible. The renewal conversation feels obvious, the expansion feels like a natural next step, and the at-risk moments get handled before they become escalations. If your customer is surprised by a renewal date, you've already lost.

That advocating for your team isn't the same as protecting them. Early in my career I'd shield people from hard feedback or tough decisions. It made me feel like a good manager. It made them weaker. The best thing you can do for someone is hold them to a high standard and tell them the truth, kindly, but clearly.

One where Customer Success is treated as a commercial function, not a cost center. One where the team has real authority over retention, expansion, and the playbooks that drive both. And one where the leadership is genuinely curious about what AI changes, not because it's trendy, but because the operating model of the next decade looks materially different from the last one.

That I'm direct, I expect a lot, and I show up. I don't believe in being everyone's friend at work, but I do believe in being someone's reason they grew. The bar I hold for myself is the bar I hold for the team.