How to Build a Customer Onboarding Program from Scratch with Cara Benecke

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Customer onboarding can make or break a customer’s entire journey—and yet, it’s one of the most overlooked areas in Customer Success. In this episode of The Customer Success Pro Podcast, I sat down with Cara Benike, Head of Customer Success and Support at Workflex, to unpack what it really takes to design an onboarding process from the ground up. From fighting for budget and headcount in a scrappy startup environment to balancing enterprise needs with self-serve customers, Cara shares a transparent look at what building onboarding really looks like behind the scenes.

Whether you’re a CSM designing onboarding for the first time or a CS leader scaling processes across segments, this episode is packed with actionable takeaways to help you drive adoption, increase retention, and create wow moments that stick.

From Sales to CS: Why Onboarding Was the First Process Cara Prioritized

When Cara first joined Workflex, she wore many hats. She was managing 70 sales opportunities and over 100 existing customers—yes, at the same time. But through that intense season, she quickly saw one pattern emerge: customers who had a strong onboarding experience were more likely to adopt quickly, stay engaged, and renew with ease.

Rather than waiting for churn issues to arise, Cara made the strategic decision to focus on onboarding first. Why? Because customers were making value judgments within hours—not weeks—of signing. By giving new customers immediate access to a demo environment and prioritizing that first wow moment, Cara helped ensure Workflex customers felt validated in their decision right away.

“There’s no such thing as a perfect onboarding. But when you start with value and listen to your customers, you’re already ahead.”

Building the Onboarding Blueprint: Feedback, Segmentation, and Customer-Led Design

One of the most powerful aspects of Cara’s onboarding program is how deeply it’s rooted in customer feedback. Rather than making assumptions, she conducted interviews with recently onboarded clients, analyzed what worked (and what didn’t), and began mapping out different onboarding tracks based on use case and segment.

Cara’s approach? Start with conversations, not checklists.

From there, she created customer journey buckets for different personas and company sizes. For smaller ARR customers (~6K), she began testing self-onboarding flows using tools like Valuecase, which served as a digital command center for new users. For larger enterprise clients, onboarding remained highly personal and consultative, with kickoff calls and high-touch support.

Her North Star remained clear: every onboarding process, whether automated or manual, had to drive measurable outcomes.

“I always ask the customer: What does success look like at the end of onboarding? What number needs to change to make this worth it?”

Scaling Strategically: Budget Battles, Tooling Gaps, and Team Motivation

Like many CS leaders in startups, Cara faced a familiar uphill battle—securing budget and headcount. While sales teams were rapidly expanding, CS was left to do more with less. To solve this, she took a data-driven approach, tying onboarding requests directly to ARR impact. This helped her get buy-in for new tools, streamline handoffs, and create operational efficiency.

She also focused on keeping her team motivated. Onboarding can become repetitive, so she rotated CSMs between onboarding and strategic account work. She gave team members ownership over improving onboarding flows and encouraged them to identify process gaps and implement changes. Even Cara jumped back into onboarding a few months ago to experience the process firsthand.

“It’s not just about scale—it’s about sustainability. You can’t just keep hiring. You need to build onboarding that grows with you.”

Lessons from the Field: What to Do (and Not Do) When Building Onboarding from Scratch

Throughout the episode, Cara shares hard-won advice for CS professionals building onboarding from scratch:

1. Don’t skip customer interviews. 

You need real insights to design real solutions. Ask your newest customers what worked, what didn’t, and what they wish they had.

2. Deliver a fast wow moment. 

Whether it’s access to a sandbox or a demo environment, don’t wait days or weeks to show value. Deliver an experience that says: “Yes, this was the right purchase.”

3. Don’t take surface-level answers at face value. 

If a customer says “we want more logins,” dig deeper. Ask how many, why it matters, and what business outcome it supports.

4. Know what can fall off your plate. 

You can’t prioritize everything. Sometimes, focusing on onboarding means pausing renewals or advocacy. That’s okay if it drives long-term retention.

5. Build for now, but plan for scale. 

Start with one onboarding process—but don’t stop there. Segment over time and evolve your approach as your customer base grows.

Key Takeaways

• Onboarding is a revenue driver not just a post-sale formality. Starting strong leads to stronger adoption, expansion, and renewals.

• Customer feedback is your blueprint. Let your onboarding design be shaped by the people going through it.

• Deliver value early and often. The first 24 hours matter more than you think.

• Use segmentation to work smarter, not harder. Not every customer needs the same touch points.

• Get buy-in through data. Tie every onboarding initiative to ARR, expansion, or retention to justify the investment.

Listen Now & Build a Scalable Onboarding Experience

This episode with Cara Benecke is a must-listen for CSMs, CS leaders, and anyone building onboarding from scratch or scaling it across customer segments.

🎧 Listen on your favorite platform:

🔹 YouTube

🔹 Spotify

🔹 Apple Podcasts

Want to win a free pair of airpod pros, sign up for a demo with Vitally: https://www.vitally.io/cspro