How to scale a sales team and reduce sales churn (ft. Chris De Vylder, CRO @ Sentry.io)
by Mohammed Shehu
Open-source software is eating the world. Customers have become increasingly frustrated with proprietary tools and the vendor lock-in that comes with them. They prefer the transparency and trust that come with the community.
Companies that are open-source-first gain an edge in this new era. Users delighted with the open-source solution convert from proprietary platforms into free or paid users of their corresponding SaaS solutions. This drives a product-led flywheel.
This is the environment that Sentry.io, the software error and performance monitoring platform, plays in. They’ve built their solution to be open-source first.
Helping us understand this evolution is Chris De Vylder, Sentry’s Chief Revenue Officer and an avid adventure traveler with over 80 countries under his belt.
He shares his thoughts on handling customer churn, integrating enterprise teams after mergers or acquisitions, and the two most important skills sales leaders need to hone.
Towards a developer-first focus: How the devtool space has evolved
As companies and institutions move their operations over to cloud providers like Azure, Amazon Web Services, or Google Cloud, they have to worry less and less about keeping their infrastructure up.
Applications scale up and down with demand and the underlying infrastructure has increasingly become self-healing.
However, incidents, errors, and performance problems haven’t gone away. Companies need to ship software faster to keep up with competition and the root cause of the problem is generally not found in infrastructure, but in the software itself.
As a consequence, the focus is shifting from operations to the developer. That’s where Sentry comes in.
When incidents occur, the key is to assess the impact to the user fast, with granular context, and to get that information as fast as possible to the only person who can solve the problem: the developer.
“To really understand what is going on with your end-user, you need to go look at it at a more granular level: What is an individual user experiencing? What are the problems they have when they use an application, platform, website, or gaming console? Then, bring these problems back as fast as possible to the developer so they can address them.” - CDV
The story of Sentry.io
Sentry’s origin story follows a well-worn path of “solving your own problem.” The founders, David Cramer and Chris Jennings, created a solution to a problem they faced, open-sourced it, then offered a paid version of it after it gathered major traction.
Today, they support 80K organizations across 146 countries and have raised over $127m in funding. They specialize in serving industries where failures have an immediate impact on revenue since competition is only a click away.
“We are big in gaming, marketplace applications, delivery applications, and other extremely competitive apps where there are tons of users. We’re still running all of our sales activities out of North America and will be expanding to Europe.” - CDV
Per Chris, there are about a million developers using Sentry’s open-source solution and over tens of thousands of paying customers as of writing.
Within those accounts, Chris’ team hunts for signals to determine which accounts would benefit most from engagement with the sales and customer success team, allowing Sentry to scale according to customer needs.
A core element of Sentry’s go-to-market strategy is account expansion — taking the initial island of users within a target company and determining which other teams could adopt the solution.
Sentry’s goal is to standardize error and performance tracking across development teams in each organization.
More recently, Sentry has also seen a number of open-source customers engage to discuss migrations to Sentry’s SaaS offerings.
“When customers who are hosting our open-source product themselves engage with us, we let them know the benefits of moving to a SaaS offering. That has become a key source of opportunities for us.” - CDV
This is the open-source migration playbook - offering a self-serve SaaS solution for those who want more support or functionality than your free, open-source version. Other notable companies using this playbook include PostHog and Grafana.
And like most of those products, part of Sentry’s appeal is its users being able to revert to its free, open-source solution if needed — and to use them in conjunction with other tools as part of their observability stack.
How Sentry leverages Slack for customer communications
Like many startups, Sentry has moved much of its customer communications into Slack — choosing to meet its core customers where they spend most of their day.
Chris has found that the real-time nature of Slack communications leads to increased trust, which helps customers openly share their needs and challenges.
When a new sales opportunity comes in, Sentry automatically opens up a Slack channel with Momentum to engage with the prospect and walk through whatever issues they may be facing, highlight their value proposition, and qualify them for paid migration.
Much of this process involves roping in the right stakeholders from other departments to weigh in on the opportunity.
“During that process, there are a lot of questions about the technical aspects of the product, licensing questions, security questions, etc. We also bring in all the different internal people that need to be involved in this, whether that’s solution engineers, the legal team, or security teams at Sentry.io. They all get put in that Slack channel so they can address the questions of the customer as fast as possible.” - CDV
Still, the company faces unavoidable challenges. While Sentry’s platform itself is localized, it faces language barriers in some of its larger markets for gaming and marketplace apps, such as Japan, Korea, and much of Asia.
Sentry aims to onboard more diverse language speakers on its sales team as it expands and scales to new territories.
How to reduce churn in enterprise sales
If your ARR is a castle, churn is the equivalent of little bricks falling off over time. This attrition can be caused by a poor user experience, a pricing-value mismatch, a better product elsewhere, or a poor customer experience with your company.
Chris’ advice for managing and reducing churn boils down to one thing: understanding and managing expectations.
“If you’re clear and transparent upfront about customer expectations and you deliver against those expectations, then churn is a non-issue. We don’t sell shelf-ware. At Sentry.io, we map out the customer’s needs and follow up closely to ensure we meet those needs.” - CDV
Understanding your customer’s needs requires nuance and an empathetic approach. It’s not enough to pepper them with interview-style questions during a discovery call.
You also need to create the space for them to share information that might challenge your solution, unearth new product ideas, and give you greater insight into the problems they and their peers face.
“Try to understand where a customer is at. That doesn’t mean interrogations — but rather based on a point of view you have about the industry that you have developed over time, combined with the ability to adapt that to a customer’s specific environment.” - CDV
It’s much easier to do this in sales-led companies where you have closer contact with the customer, as opposed to product-led companies where the customer is far removed from the sales team and may not voice their frustrations until it’s too late.
This is because, in both scenarios, internal roadblocks may hamper adoption within your target companies.
While organic growth and adoption are especially desirable for product-led companies, internal approval processes and compliance requirements may come up against the value that your solution provides.
A key aspect of running a PLG go-to-market strategy is making proactive efforts to engage with those internal stakeholders and ensure nothing goes off the rails for them.
“As you grow bigger in these accounts, there are other people that have concerns about it. Security is an obvious one. If internal security teams haven’t signed off on things or looked at certain aspects of the product, there is a risk that some of that starts to disrupt your relationship.” - CDV
How to integrate enterprise teams after a merger or acquisition
Each year, a large number of companies report feeling that their integration wasn’t a success — either due to slowed momentum, poor employee engagement, management clashes, tech stack integration failures, or cultural shifts in one or both entities.
Having worked through more than five acquisitions throughout his career, Chris’ advice for RevOps and sales leaders going through a merger or acquisition echoes his earlier tips on reducing churn: manage expectations by articulating what’s negotiable and non-negotiable upfront, then communicate that in all your marketing, sales, and customer engagement motions.
One example here relates to Atlassian’s stance on pricing. As the previous Global Head of SMB Sales at Atlassian, Chris shared that many of the companies Atlassian acquired had little to no transparent pricing.
However, within six weeks of an acquisition, Atlassian would review the acquired company’s offerings, determine the right price points for them, and put those prices up on their website.
Atlassian also never negotiated pricing terms with customers, and all new acquisitions followed suit shortly after joining the stable.
Success here involved educating the sales team on the benefits, not just for them, but for the customer, which ultimately reduced the back and forth during deal negotiations and shortened the sales cycle.
“Negotiations around discounting and terms are generally all oriented towards, “Am I getting a decent deal?” And transparency solves that because they know they get the same deal as everybody else. If you stick to that, it increases trust for the customer.” - CDV
Integration is a two-way street, and the host company can also draw useful business workflows and approaches from the acquired company to apply to their organization. The key here, again, is to constantly communicate this change across the organization.
“If you want to take something in an acquired company and make that a standard practice in a larger company, there are a number of things you need to do in terms of training, enablement, and communications.” - CDV
Most importantly, says Chris, treat your newly acquired employees like they’ve been your employees forever.
While maintaining team structures can be challenging post-acquisition, you’re likely getting a team with many years of deep experience in their line of work.
Rather than downsizing acquired teams as a cost-cutting exercise, consider how to expand their roles or level up their careers within the host company or the acquired one.
Sales leaders: Build these two core competencies
There are two skills sales leaders need to master: over-communication and hiring.
You’ve heard it before, but it bears repeating: consistent communication is key to a successful sales career. This point grows even more important as a company matures and scales its operations, introducing new friction to the mix.
Communication isn’t just for internal teams. The most successful salespeople are those who understand their customer’s needs and can communicate the impact of their solution in a helpful, respectful way that avoids pushy sales tactics or creating false urgency.
“People want to buy your product because they will be better off after they do so. That ability to really understand what’s going on, articulate how your solution will solve their challenges, and convince the customer is what a modern salesperson needs to be able to do.” - CDV
And of course, hiring remains a core skill for sales leaders to hone - especially if they expect fruitful tenures at the top.
Hiring mistakes are unavoidable, but having the right frameworks in place for finding, filtering, interviewing, offering, and onboarding new candidates leads to lower attrition, happier and more engaged employees, and a more productive workforce.
Curiosity is a precursor to empathy in the sales process - something Megan Smith of HubSpot prioritizes - and perseverance helps sales reps weather the inevitable rejections they will face. And like Vandana Nair (ex Workday), arrogance ranks high on his list of red flags.
“If you try to convince somebody to buy something or to teach them something about their business, there has to be some level of confidence, but you want to make sure that that doesn’t turn into arrogance.” - CDV
Reduce churn and build a scalable team today
Enterprise growth boils down to gaining a deep understanding of your customer’s needs and changes in the market, and communicating the value you can bring to their bottom line — both to decision-makers and your own sales teams.
Communicating expectations — whether around benefits, pricing, or team deliverables — underpins much of the valuable work of savvy sales leaders.
And as long as this approach applies equally to hiring, acquisitions, sales, and marketing, success is almost guaranteed.