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Maximizing Growth Through Customer Success - With Jameson Braddock, VP of CS at Rently

Last week we had a conversation with Jameson Braddock, Vice President of Client Success at Rently, a company that provides self-guided tours and smart home technology for the real estate industry. Jameson's unique background in sales engineering and his experience across various company sizes brings a fresh perspective to client success. Here's what we learned:

Maximizing Growth Through Customer Success - With Jameson Braddock, VP of CS at Rently

Last week we had a conversation with Jameson Braddock, Vice President of Client Success at Rently, a company that provides self-guided tours and smart home technology for the real estate industry. Jameson's unique background in sales engineering and his experience across various company sizes brings a fresh perspective to client success. Here's what we learned:

Can you tell us about your background and your role at Rently?

Jameson: I started in the startup world where we had about 5-15 people, and we grew that company until it sold to a larger company called Paylease. From there, I got to work with Vista Equity and learned about some of the best practices for both support and success. Then we got acquired again by Global Payments, so I got to see how real high-level, large companies are run.

At Rently, we do self-guided tours, smart home technology, and other products. On the client success side, we're split into three different teams: a multifamily team, a single family team and a couple of support teams that I also run.

How has your sales engineering background influenced your approach to client success?

Jameson: Having a sales engineering background has helped out a lot. When I look at the client success team, it's about knowing the product and knowing it really, really well. I think having that background allows me the ability to really dig deep into understanding the engineering lingo and what's going on in the background with the integrations.

It's especially helpful when communicating with the product team. We have instances where we'll go directly to engineering on some items or tasks, and the communication flow is good. I wouldn't say our integrations or products are that complicated, but my background has allowed me an opportunity to communicate effectively across teams.

How do you manage the different needs of your various customer segments?

Jameson: It's tough. Each vertical is different in what they need and want. We're pretty old school in our approach. We'll have sheets with feedback. We use Gong, so there's a lot of recording and items there.

Typically, we'll push a product or an idea, and then we'll gather as much feedback as we can from that section or group. We run campaigns, essentially. If we're trying to do a strategy with pricing or a new product, we'll probably start off with a nice subset of a group. We might go regionally - for example, we might say we're going to attack Texas first. So we'll go after 30-40 accounts in Texas, get the feedback, change our positioning and messaging based on what we hear, and then push to a larger market. Once we feel good about it, we'll do it on a large scale.

How does your team approach upselling and expanding accounts?

Jameson: One thing that we do a little bit differently here is that we have it set up almost like an SDR model. The way we're commissioned and our goals are set are all about opportunity generation and getting it over to a sales rep. All expansions and upsells go through the account executives (AEs), even if it's a relatively straightforward deal.

We discovered that there were just so many gray areas in that process that we decided to make it black and white. This strategy allows our client success team to focus on generating opportunities without the pressure of closing deals.

How do you identify upsell opportunities?

Jameson: We have certain keywords and things that we look for to be able to push certain products. For example, on the single-family side, security is a really important thing. If we hear anything about security or issues regarding security, that's an instant trigger for us to introduce our three security products.

This can come from a conversation or even a support case. If we're seeing a lot of security-related issues on the support side, that's a trigger for us to reach out to them, show them our security offerings, and tee up an opportunity.

How do you maintain a high-quality team with typically high-turnover roles?

Jameson: We have different approaches for our teams in India and the US. For our India teams, which handle most of our support and some SMB accounts, we have a two-year contract that new hires sign when they join. This reduces the number of people coming in, but we have a good culture out there and I think the office is amazing.

The second key is career pathing. We set up a clear progression, like CSM to Senior CSM to Enterprise CSM, and then show the path to becoming a team lead. As you move up, you get a certain number of enterprise or core clients. We also have a pretty good commission plan.

Lastly, we develop a culture of wanting what's best for our employees. If they want to transition to sales or another department, we support that. We've almost taken on the culture of being the "minor league" - we know this is where we grow and retain talent, and we're going to bring them to other places within the company to grow.

So what did we learn?

Talking to Jameson was a great insight into how a modern client success team can operate effectively across different customer segments while also driving growth. Here are the key takeaways:

1. Leverage technical knowledge: A background in sales engineering or product can help you communicate more effectively with both customers and internal teams.

2. Test and iterate: Start with small campaigns to test new products or strategies, gather feedback, and refine before rolling out to larger markets.

3. Align success with sales: By focusing client success teams on opportunity generation rather than closing deals, you can create clearer roles and potentially increase overall sales.

4. Listen for upsell triggers: Train your team to listen for specific keywords or issues that indicate an opportunity for upselling or cross-selling.

5. Invest in career development: Clear career paths, good compensation, and opportunities for internal mobility can help retain talent in typically high-turnover roles.

By applying these principles, companies can create a more effective client success function that not only supports existing customers but also drives growth. As Jameson put it, "We've almost taken on the culture of being the 'minor league' - we know this is where we grow and retain talent." It's about creating a culture where customer success is seen as a crucial part of the overall business strategy, not just a support function.