← Back to all posts

Scaling Customer Success with Data-Driven Strategies: Insights from Becca Weiss at Flatfile

Last week, I had the opportunity to speak with Becca Weiss, VP of Customer Success at Flatfile, a data onboarding platform. Becca's unique approach to scaling customer success and support in a high-growth startup environment offers valuable lessons for CX leaders across industries. Here's what we discussed:

Scaling Customer Success with Data-Driven Strategies: Insights from Becca Weiss at Flatfile

Last week, I had the opportunity to speak with Becca Weiss, VP of Customer Success at Flatfile, a data onboarding platform. Becca's unique approach to scaling customer success and support in a high-growth startup environment offers valuable lessons for CX leaders across industries. Here's what we discussed:

Can you tell us about your background and your current role at Flatfile?

"I started my tech career in customer support, though I initially thought I was going to be a speech pathologist. I began at SendGrid, where I learned that I enjoyed relationship building and de-escalating tense situations. This led me to move into customer success, starting with an implementation team role.

When Twilio acquired SendGrid, I was given the opportunity to lead implementation for all of Twilio's core products. This was a huge learning opportunity, allowing me to apply what we'd learned at SendGrid to Twilio's larger scale.

After about two and a half years at Twilio post-acquisition, Flatfile reached out to me. I saw it as an opportunity to apply everything I'd learned over the past seven years to a new company. I've been at Flatfile for almost three years now, overseeing customer success, support, and what we call solutions engineering."

How does your approach at Flatfile differ from your experiences at larger companies like Twilio and SendGrid?

"At Flatfile, we've had to be more innovative and efficient with our size team. We recently shifted to a more product-led growth (PLG) model, which presented new challenges. We went from having dedicated customer success managers for key accounts to managing a larger number of customers with a smaller team.

One significant difference is our approach to support. We have a concept we call 'radical support' at Flatfile. Essentially, we're trying to move our customers forward in a way similar to customer success, but within the support motion. Our support team doesn't just solve immediate issues; they proactively engage customers about new features or opportunities to get more value from our product.

We actually don't think more tickets are bad; we think that more tickets mean more engagement. We do things to make our customers want to engage with us. This approach has led us to look at support metrics differently. Instead of focusing solely on ticket closure time, we track what we call 'engagement drivers' - instances where our support team has moved the customer forward in some way."

How do you manage to scale support with such a small team?

"We have a two-person support team handling about one hundred tickets daily. We've been able to scale without adding more people through several strategies:

1. Automation: We're building an internal tool that will automatically create engineering tickets based on support interactions, saving our team time.

2. Focus on engagement: Our target is for 40% of our tickets to become 'drivers' - opportunities to engage customers beyond their immediate issue. In support, we don't use chatbots at all. Our volume is manageable for our small team but still a significant workload.

  • We're building out a custom app in Front, our support tool, that will automatically surface relevant customer information to our support agents. This allows them to easily identify opportunities for engagement and upsell without having to search for it.

  • While we don't have concrete metrics yet on the business impact of this approach, we're tracking it closely. We implemented this more structured 'driver' approach in January, so we'll have a full year of data by the end of this year. My theory is that we're going to see Net Revenue Retention (NRR) increase for the group of customers who had tickets that were drivers, compared to the rest of the customer base. 

3. Channel optimization: We don't do phone support at all. Our customers are mostly developers who prefer Slack and email communication.

4. Data-driven decision making: We're using the data from our 'radical support' approach to inform when we need to scale the team. If our 'driver' percentage starts to dip below 40%, that's when we'll consider adding more support staff.

5. Leveraging technology: We use a tool called Front for our support, and we're building custom apps to surface relevant information to our support team automatically."

How do you use customer feedback to drive strategic decisions?

"I talk to customers all day long, and it's challenging to know when individual feedback represents a broader trend. Recently, we've been migrating customers from a legacy product to a new version with a different pricing model. To understand the impact, I personally reached out to a subset of customers for in-depth interviews.

We're using the data from these interviews to inform our pricing model and product strategy. It's about combining gut instinct - knowing which issues are worth diving into - with structured data gathering. By interviewing a specific subset of customers, we can identify themes and trends that might not be apparent from individual feedback.

This approach allows me to go to our product and marketing teams with concrete data about how our pricing model should work based on what our customers and prospects are saying. It's a way of bridging the gap between anecdotal feedback and data-driven decision making."

So what did we learn?

Becca's insights highlight several key principles for scaling customer success and support in a high-growth environment:

1. Redefine support metrics: Instead of focusing solely on traditional metrics like ticket closure time, consider metrics that reflect customer engagement and growth.

2. Leverage automation wisely: Use technology to automate repetitive tasks, allowing your team to focus on high-value interactions.

3. Embrace a 'radical support' mindset: Train your support team to proactively identify opportunities to drive customer value, not just solve immediate issues.

4. Balance gut instinct with data: Use your experience to identify important issues, but validate and explore them through structured data gathering.

5. Optimize for your audience: Understand your customers' preferences (like developers preferring chat over phone support) and tailor your approach accordingly.

6. Turn support into a growth driver: By focusing on engagement and proactive support, you can potentially drive revenue and retention through your support interactions.

7. Stay close to the customer: Even in a leadership role, maintain direct contact with customers to keep a pulse on their needs and experiences.

By applying these principles, companies can create a more efficient, effective, and growth-oriented approach to customer success and support. As Becca put it, "We don't think more tickets are bad; we think that more tickets mean more engagement." It's about creating a culture where every customer interaction is an opportunity to drive value, both for the customer and the business.