Finding Your Next Role in Customer Success

The Reality of Cold Applications in 2025
Chris and Jason are blunt: cold applying to job boards without doing anything else is not a winning strategy. "So many companies get inundated with hundreds and hundreds and hundreds of applications for an individual role," Jason explains. "It's tough to cut through the noise at that point." While some people do land roles through cold applications alone, the hosts emphasize that leveraging your network dramatically increases your chances of getting noticed and moving forward in the interview process.

Your Network is Your Superpower
Both hosts landed their recent roles through connections they had built throughout their careers. "The last three jobs that I've gotten in my career have been through my network," Jason shares. Whether it was a college friend who became a recruiter, a former manager who vouched for his work, or maintaining relationships with colleagues after leaving organizations, these connections opened doors that cold applications could not. The key lesson: do not let relationships fade when you or someone else leaves a company. Those connections could be the difference-maker in your next job search.

Leveraging Your Unique Customer Success Advantage
Jason points out a strategy many CSMs overlook: "Customer success is positioned in a very unique way where we can kind of understand what's happening with our customers' businesses." If you have built strong relationships with champions at your customer accounts, those connections can be a pathway into a new role. You already understand the organization, you can speak to what they do, and you have demonstrated your ability to drive value. It is an often-underutilized inroads that CS professionals should consider.

Making Your LinkedIn Outreach Count
Chris addresses a common mistake he sees: generic referral requests. "If you're reaching out to somebody who you've worked with, but maybe haven't had that relationship that has kind of sustained," he advises, "doing that personalization and also helping them feel more confident in advocating for you" is essential. Generic messages like "Can you refer me?" put the recipient in an awkward position without giving them ammunition to actually advocate for you. Instead, Chris recommends highlighting your accomplishments, quantifying your success, and explaining specifically why you are interested in that company. Give the person enough material to feel confident vouching for you.

What to Look for in Your Next Company
Jason's top priority when evaluating Vanta was growth opportunity. "Looking for a company that was really kind of growing quickly and has that room for growth," he explains. "I think sometimes it's very easy to find yourself becoming stagnant with where you are." He recommends looking for signals like funding rounds, massive hiring, and segment growth opportunities. Chris focused on finding a company where he could actually deliver on customer needs, saying about Clay: "I really think that's where Clay is killing it today."

The Due Diligence Questions That Matter
Beyond the surface-level research, Chris emphasizes asking tactical questions during the interview process: What does the book size look like? How many customers will you manage? What are the clear goals for the team? Are they hitting them? These questions help you understand what your day-to-day will actually look like and whether the role sets you up for success.

Book Size: Important but Don't Overindex
Jason offers nuanced advice on evaluating account loads. "CSMs can over index on" book size, he cautions. The real question is: what are the expectations for customer engagement? A 70-account book might be manageable if you are only doing monthly check-ins post-implementation. But if the expectation is weekly tactical calls and hands-on workflow setup, you probably want 20 accounts or fewer. Context matters more than the raw number.

On Interview Preparation:
"I really focus on having multiple stories, whether that's like save stories, success stories of customers you've grown," Chris shares. "I also like to prepare myself with the inverse... talk me through a turn where you feel like you had fault." Being ready to discuss both wins and failures shows humility and self-awareness that interviewers value.

On Discussing Failures:
Jason emphasizes that recruiters care more about how you respond to failures than the failures themselves. "Recruiters at that point won't focus so much on the fact that you failed. They'll focus more on the fact that, like you created a plan to save it. You created a plan to try and come back from that. And that shows a lot of grit."

On Leaving Your Current Role:
"Being able to articulate that story in a way that shows, okay, like I gave this a fair shake. I tried to make this work," Jason advises. Then pivot to what excites you about the new opportunity. Frame your departure professionally while showing genuine enthusiasm for where you are heading.

On Green Flags:
Chris's biggest green flag is cross-functional collaboration. "They're involved, that customer success for them looks like a team sport and something that the entire organization is involved in." The biggest red flag? When everything falls on the CSM alone.

On the AI Red Flag:
Jason warns about companies overselling AI as a CS solution. "If I'm going into an organization and I'm hearing them saying, hey, you're gonna manage 150 accounts, but you're gonna do it with AI and it's gonna be great, massive red flag." While AI can be a great complementary tool, it cannot yet replace the human relationship-building that is core to Customer Success. "CSMs are still needed. AI isn't at the point where it can run a relationship. It's not at the point where it can build trust with a customer."

Create a short list of companies you genuinely want to work at, then prioritize personalized outreach to your connections there.

When reaching out for referrals, quantify your accomplishments and explain why you are excited about that specific company.

Maintain relationships with former colleagues and managers — do not let those connections go cold.

Prepare multiple success stories and failure stories before interviews, with specific numbers and outcomes.

Ask tactical questions about book size, goals, team performance, and day-to-day expectations during the interview process.

Look for companies with visible growth signals: funding rounds, hiring sprees, opportunities to move up-segment.

Be ready to explain why you are leaving your current role in a professional way that highlights what you tried to accomplish.

Watch out for roles where everything falls on the CSM.

Be cautious of companies that position AI as a replacement for CSMs rather than a complement to the role.

Follow up with everyone in the interview process — run it like a sales process with thank you emails and LinkedIn messages.