The Journey: #011 The Next 90 Days

When I stepped into my role as a new VP of Customer Success, the welcome was overwhelming—in the best way possible.

My inbox flooded with “So excited you’re here!” messages. My calendar was packed with meet-and-greets, each one filled with eager faces nodding in agreement as I laid out my ideas.

The first 90 days were a dream. Everything felt possible. I was listening, learning, building trust, and setting the vision. My first board meeting was engaging and supportive. The team was aligned, the CEO was excited, and I felt unstoppable.

And then, the next 90 days arrived.

The same people who had once embraced my ideas with enthusiasm started pushing back.

"That’s not how we’ve done it."

"We don’t have the resources for that."

"Do we really need to change this?"

I was no longer the shiny new leader full of promise—I was the person responsible for delivering results.

The energy had shifted from excitement to expectation. The grace period was over.

If you’re a new CS leader, this transition from possibility to proof is where things get real.

Here’s how to navigate the next 90 days, where your success is no longer defined by what you plan to do, but by what you actually do.

Five Ways to Win the Next 90 Days

1. Focus on Quick Wins That Build Momentum

Big transformations take time, but momentum is everything. Identify 2-3 high-impact, low-effort wins that show progress quickly. Maybe it’s refining your renewal process, launching a simple customer health score improvement, or eliminating an inefficient meeting draining your team’s time. Show that you can execute—not just ideate.

What I tackled first:

✅ Built a centralized repository for customer data

The CSM team lacked a single source of truth. Customer insights were scattered—some in SFDC, some in spreadsheets, but nothing cohesive to help them proactively manage accounts. I identified a solution, secured buy-in, and deployed it. This shifted the CS team from reactive to proactive-ish and gave us the visibility needed to truly run the business.

✅ Invested in upskilling the team

While the team had the will, many lacked the skill. I brought in SuccessCoaching to train them, giving them the tools and frameworks to be true strategic partners to our customers.

✅ Identified and mitigated revenue risks

I mapped our largest renewals for the year and pinpointed three major accounts that, if lost, would significantly impact our targets. Partnering with CSMs, leadership, and product, we built a plan to re-engage those customers. We preserved almost all the revenue.

2. Turn Resistance into Buy-In

Pushback isn’t rejection—it’s an invitation to prove your case. Instead of seeing resistance as a wall, treat it as a window into what people value and fear. Ask questions. Dig into the why behind the hesitation. People aren’t against change—they’re against uncertainty. The more you involve them in shaping the solution, the less resistance you’ll face.

What I tackled first:

✅ Redesigning a failed initiative

One of my recommendations—a structured Feature Idea workflow—was met with strong resistance. Leadership had tried a version of it before, and it had failed. Instead of pushing forward blindly, I dug in. I learned what had gone wrong the first time and redesigned my approach to address those gaps. By educating and collaborating with stakeholders, we turned skepticism into support.

3. Balance Quick Decisions with Long-Term Strategy

The pressure to perform in these next 90 days is intense. You’ll be tempted to make fast decisions just to show impact. But reactive leadership rarely builds sustainable success. Keep your long-term vision intact while making smart, tactical moves that create immediate value.

What I tackled first:

✅ Creating a culture of collaboration

One of the biggest complaints I heard was the lack of cross-functional alignment. So I introduced a weekly CS team meeting with a rotating guest function—Marketing, Sales, Product, Services. This small shift required minimal effort but drove meaningful collaboration and visibility across teams.

4. Manage Up with Ruthless Clarity

Your CEO, CRO, and board don’t just want updates—they want outcomes. Clearly articulate where things stand, what’s working, and what roadblocks exist. More importantly, frame your updates in terms of business impact, not just CS metrics.

❌ “We improved onboarding NPS by 20 points.”

✅ “We reduced time-to-value by 30% and unlocked $500K in expansion opportunities.”

What I tackled first:

✅ Establishing a clear revenue strategy

I needed a baseline of our CS business metrics to assess where to focus. One immediate opportunity? We weren’t enforcing our true-ups, leaving money on the table. We designed a process and messaging strategy to ensure proper invoicing, boosting NRR. When you drive revenue impact, you get attention—the good kind.

5. Protect Your Confidence & Energy

This phase is mentally and emotionally exhausting. You will question yourself. You will feel the weight of expectations. The best leaders don’t just manage customers and teams—they manage themselves. Set boundaries, protect your thinking time, and don’t let short-term turbulence shake your long-term conviction.

What I tackled first:

✅ Secured a mentor

This company had never had a formal CS leader before, and I knew I’d be navigating a lot of firsts. Having a mentor allowed me to pressure-test my ideas, refine my approach, and ensure I wasn’t operating in a vacuum.

✅ Established a morning focus routine

I’m a morning person, so I got to the office early and spent the first part of my day on strategy, not just execution. This gave me the mental clarity to work on the business—not just in it.

Final Thought: Leadership Isn’t a Honeymoon—It’s a Marriage

The first 90 days are like dating—you’re impressing, exciting, and dreaming big. But the next 90? That’s where the real work begins.

This is where you prove you weren’t just a great hire—you’re the right leader for this team, in this company, at this moment.

The transition from excitement to expectation isn’t a sign that you’re failing—it’s a sign that you’re now accountable. And that’s exactly where you need to be.

Welcome to real leadership. Now go make it happen.