Career Changes from Salesforce to Twilio to CockroachDB

By Published On: June 28, 2023

About the session

This episode features a conversation between Keith Townsend and Kevin Schwaba, an account executive for Cockroach DB. They discuss Kevin’s career journey, his experiences working in different sales roles, and the challenges and insights he has gained along the way. It’s a unique journey from talking to direct business value to the business value of infrastructure.

The CTO Advisor
The CTO Advisor
Career Changes from Salesforce to Twilio to CockroachDB


– Kevin’s career journey and experiences in different sales roles

– Transition from business value conversations to more technical sales

– Challenges and insights gained from working with different types of customers



Takeaway 1: Transitioning from a business value-focused role to a more technical role can be both challenging and rewarding


Kevin Schwaba shared his career journey from working at Salesforce, where he focused on business value conversations, to Twilio, where he had to acquire more technical knowledge to build trust with developers. He emphasized the importance of understanding how APIs work and learning about the unique aspects of telecom in order to succeed in a more technical role.


“At Twilio, I had to build some expertise in how these APIs worked,” said Schwaba. “I was used to kind of going in there the one day, getting a feel for this person who really wants the car, kind of using that emotional intelligence to kind of get their confidence up and sign on the dotted line. And now all of a sudden I’m selling this huge engine within a jet and explaining how the RPMs work and really getting nuts and bolts of how it all happens.”


Schwaba also mentioned the enjoyment he experienced while working on projects that involved building together and helping customers build a proof-of-concept. This hands-on approach allowed him to hone his technical skills and better serve his clients.


Takeaway 2: Adjusting the perspective on business value when selling to different groups within the value chain


In his transition from Salesforce to Twilio, and eventually Cockroach DB, Schwaba discovered the importance of adjusting his perspective on business value depending on the target audience. While at Salesforce, he focused on business leaders, but at Twilio and Cockroach DB, he had to engage with developers and engineers, respectively.


“It’s business value, but the lens is very different,” explained Schwaba. “There could be efforts to shard. So you’re trying to scale your database, but when you shard and you do those manual types of things, it makes the builders jobs harder because every time they have to do a release, every time they want to build a new feature application, they’re having to add more work because of the Sharded database.”


Schwaba emphasized the need to understand the unique challenges faced by different groups within the value chain and adjust the business value conversation accordingly in order to effectively communicate the benefits of the solution being offered.


Takeaway 3: Emphasizing the core impact of a solution on a customer’s business


When selling a solution like Cockroach DB, Schwaba highlighted the importance of understanding the core impact it can have on a customer’s business, especially when dealing with tier zero or tier one applications. He shared an example of how an outage at a gaming company could have significant effects on their brand, transactions, and SLAs, making the need for a robust and scalable database more critical.


“These SQL databases, there’s different types of databases out there. There’s the NoSQL stuff and the SQL stuff. Cockroach DB is more focused on distributed SQL. So data that has to be consistent and correct,” said Schwaba.


By focusing on the core impact, Schwaba was able to better articulate the value of Cockroach DB to potential customers, even when dealing with more risk-averse or technically-focused groups. This approach allowed him to effectively address their unique concerns and demonstrate the benefits of the solution.


Insights surfaced

1. Transitioning from business value conversations to more technical sales requires building expertise in how the products work and understanding the customers’ needs.

2. Working with developers and helping them build proof of concepts can be a fun and rewarding experience.

3. Selling core infrastructure like databases can be challenging due to the risk involved and the pressure on engineers to ensure everything works correctly.


Key quotes

1. “I realized that my key to being successful there was I’d still have to have those business value conversations, but I couldn’t lead with it.”

2. “It’s really fun to be in a sales cycle where you’re helping to have another company build it.”

3. “It’s very, very technical. I’ll admit I’m still learning a lot in the role.”

4. “It’s interesting to see how you can do that and how it tends to be with a lot of these kind of newer companies, you’re going to be able to just build things a little bit better often because it’s been built in a newer way.”

5. “There’s a lot of risk tolerant types of conversations within it that just weren’t there if salesforce didn’t work.”

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