Interview Questions I've Already Answered

Want to get a jump start on matching me to your BIGGEST CS/CX goals? Take a look at these questions I've already answered....

Career & Experience

Q: Tell me about yourself.

A: I’m Steven Sakadales, a Customer Success leader with over 15 years of experience growing Fortune 500 accounts. I've combine empathy and rigor to deliver over 250 negotiated renewals totaling over $107M in ARR. Beyond work, I’m a life coach, English Channel swimmer, and father of 3 — resilience and purpose guide my approach.

Q: What have you been working on recently?

A: I’ve been focused on deepening my professional development — refining my Customer Success frameworks, publishing thought leadership on LinkedIn, and coaching others. I’ve also been designing a personal brand project called ‘Love & Process,’ which captures my philosophy on CS leadership and life.

Q: What’s an accomplishment you’re proud of?

A: At Regrello, I managed a “too big to fail” account representing 62% of the company's total ARR. With no formal support structure in place, I rebuilt trust, created a cross-functional cadence, and grew the account by 536% in one year. That experience reinforced my ability to stabilize and expand even the toughest accounts.

Q: What’s an example of scaling processes in CS?

A: At Showpad, I led the North America CS org covering $65M ARR. I implemented enterprise-grade CS processes, standardized success plans, and built an EBR framework that improved executive alignment across accounts. These processes scaled predictably and improved retention.

Q: Why are you considering a career transition now?

A: After growing our flagship Fortune 100 customer by 536%, our startup, www.regrello.com, was acquired by SalesForce. I am looking for an AI focused company who needs true Enterprise experience in their Customer Success org.

Customer Success Strategy

Q: How do you handle a challenging client relationship?

A: First, I listen deeply. Conflict usually stems from misaligned outcomes, not personalities. I bring the conversation back to value — what the customer needs to achieve and what we’ve committed to deliver. I establish a structured recovery plan, but I never lose sight of the human relationship.

Q: How do you measure success in your accounts?

A: I look at three layers: leading indicators like adoption and engagement, lagging indicators like renewal and NRR, and human indicators such as whether executives call me before making major decisions. When all three align, I know we’re successful.

Q: How do you partner cross-functionally?

A: I collaborate proactively with Sales, Product, Engineering, and Support. Success doesn’t happen in a silo — it requires aligned incentives. I share customer insights upstream and help ensure the whole company is accountable to customer outcomes. Customer Success is the HEART of any organization wise enough to invest. Every member of the Org is part of the CS team.

Q: How do you handle working with a difficult team or Account stakeholder?

A: I seek first to understand. I listen, find common ground, and align on shared goals. If views diverge, I propose solutions instead of just criticism. My goal is always to maintain trust and keep forward momentum.

Q: How do you reduce churn in a strategic enterprise account?

A: I focus on leading indicators, re-establish executive alignment around value, and right-size the success plan. I partner to create a "North Star" goal with the customer. A set of OKR's that help guide all or our account decisions. I also remove friction fast and set up a short-term, cross-functional triage to stabilize usage and sentiment.

Q: How do you use data to make decisions?

A: I use data to separate signal from noise. The "usual" adoption metrics are not always the best indicators of Business Value. I look for leading indicators of adoption, map them to lagging indicators like renewals, and frame the insights in a value narrative. Data gives us credibility, but meaning comes from connecting it to outcomes.

Q: What’s your approach to executive business reviews (EBRs)?

A: I see EBRs as more than quarterly check-ins — they’re opportunities to reframe the value story. I get explicit agreement to have the Executive level sponsorship in the room. Then I use data and narrative together, connecting metrics to strategic outcomes. That keeps executive sponsors engaged and aligned. Also a true partnership with the daily Stakeholder to do most of the EBR presentation themselves. A great EBR is a chance for the Customer Stakeholder to showcase their work to their own leadership.

Q: How would you scale Customer Success at a startup?

A: I’d start by defining the customer journey, identifying key customer touch points (Operating Rhythm), and instrumenting leading indicators. Then I’d build lightweight processes, create a playbook with Internal Cross Org alignment, and layer in tech like Gainsight or ChurnZero as scale increases.

Future Vision & AI

Q: How do you see AI impacting Customer Success?

A: I believe AI will amplify, not replace, Customer Success. AI can handle summarization, data analysis, and scheduling — but trust, empathy, and influence remain deeply human. The future is AI + human, not AI instead of human. Here is a link to an Article I've written on this topic called "Why The Human CSM Will Thrive in an AI Driven Future".

Q: How would you use AI in your work?

A: I’d use AI to free up time from administrative work: summarizing calls, generating success plan drafts, or surfacing risk signals from usage data. That allows me to focus on strategic conversations with executives and building trust. Here is a link to an Article I've written called "How AI Helps CSM's DO What Humans Do Best."

Personal & Character

Q: Can you give me an example of your grit?

A: When I trained to swim the English Channel, it required over a year of preparation, countless hours in cold water, and unwavering discipline. I applied the same perseverance to my work with large accounts — staying the course, no matter how tough the challenge.

Q: What book has influenced you most?

A: The Infinite Game by Simon Sinek. It reminded me that Customer Success isn’t about winning one renewal or expansion — it’s about building enduring trust and value, playing the long game.

Q: What might surprise me about you once you’re on the team?

A: You might be surprised to learn that beyond expanding Fortune 500 accounts, I swam the English Channel and completed Ironman triathlons. These experiences taught me grit and perseverance — the same qualities I bring to my work.

Q: What are your greatest strengths?

A: I excel at building trust with executives, aligning teams around measurable outcomes, and scaling Customer Success processes. My blend of empathy and rigor creates results that last.

Q: What’s a weakness you’ve had to work on?

A: I can get wrapped up in details because I want to deliver the best. Over time, I’ve learned to channel that into structured delegation and prioritization so I stay strategic without losing precision.

Q: What would your best friend say are your strengths?

A: They’d say I’m resilient, curious, and deeply committed. I’m the one people call when they need someone steady under pressure.

Q: What do you do outside of work?

A: I’m a Heroic Certified Life Coach, classically trained violinist, Ironman finisher, and English Channel swimmer. These pursuits keep me balanced, disciplined, and always learning.

Philosophy & Leadership

Q: What is the most important lesson you’ve learned as a leader?

A: That trust outperforms individual brilliance. Early in my career, I thought being the smartest was enough. I learned that building trust and empowering others achieves far greater results.

Q: What motivates you as a leader?

A: I connect my work to purpose. Inspired by David Brooks’ Second Mountain, I see Customer Success as a calling to serve others and help them succeed. That sense of purpose keeps me energized.

Q: What’s your leadership style?

A: I describe myself as a player-coach. I roll up my sleeves to solve problems directly with customers, but I also mentor and elevate my team. I believe trust multiplies outcomes: when people trust you, they follow your lead and deliver their best.

Q: What’s your philosophy on Customer Success?

A: I believe Customer Success is about pairing love and process. The love is empathy — really understanding customers as people, building trust, and being a true partner. The process is rigor — success plans, executive business reviews, measurable outcomes. Without empathy, you don’t earn influence. Without process, you can’t scale. Together, they create predictable, lasting impact. The North Star of any great CS org is to create "Referenceable Customers".

Q: How do you develop high-performing teams?

A: I focus on creating clarity of purpose, aligning individuals to measurable outcomes, and building psychological safety. When people know the goal, trust their leader, and feel safe to innovate, performance accelerates.

Q: How do you approach change management?

A: I believe change requires transparency, ownership, and empathy. I over-communicate the “why,” involve stakeholders in shaping the “how,” and create short-term wins to build momentum. My role is to steady the team through uncertainty.

Compensation

Q: What are your compensation requirements?

A: I do my research and aim for a range aligned with both the market and the responsibilities. For me, compensation should reflect impact delivered and growth potential. I value roles where compensation includes base, bonus, and equity in line with accountability.