Q&A with Sarah Caminiti, VP of Customer Success at DNSimple

Q&A with Sarah Caminiti, VP of Customer Success at DNSimple

Meet Sarah Caminiti, a visionary VP of Customer Success at a thriving bootstrapped SaaS company, who brings two decades of experience in transforming the way support roles impact business success. Despite not having a traditional college degree, Sarah's journey is a testament to how perseverance, strategic leadership, and a deep commitment to customer satisfaction can carve out an extraordinary career path. At the core of her success is a profound belief in making a difference through supportive leadership, which she has demonstrated in various roles from executive assistance to leading support teams within the SaaS industry. Her innovative approach to customer success has made her instrumental in her current company, significantly boosting client retention through a meticulously crafted support experience. Beyond her professional achievements, Sarah is the brain behind The Kindness Initiative, a leadership program designed to foster more empathetic, honest, and effective management practices. Balancing her hectic life with hobbies like quilting and interior design, Sarah lives in Providence, RI, with her family, embodying the essence of a leader who not only excels in her career but also enriches the lives of those around her.

Q: What inspired you to create The Kindness Initiative, and what impact has it had on your leadership style?

The Kindness Initiative began as an opportunity to reflect on my leadership journey. Through this I realized what I’ve learned could be the nudge others need to be the leader they really want to be. I’ve had the opportunity to connect with some of the most passionate and intelligent professionals because of the The Kindness Initiative. I help them pause and look at situations from different angles and build a foundation with those they lead where everyone feels valued and included. 

How many of us have had jobs where the environment is so rooted in toxicity and we’ve been stuck with managers that lean into all the negative stereotypes we’ve seen in the movie? Probably everyone. To be fair, these managers have learned how to lead from bad bosses, and the cycle goes on and on. When I joined DNSimple, I finally saw a shift. My boss, our CEO, Anthony Eden showed me that kindness does have a place at work, and the team is better because of it. So I made a conscious effort to be the leader I always knew could exist.

I approach leadership much like I do when I’m helping customers, but treating my team and anyone I’m working with, the way I want to be treated. I’ve had some bumps, but I’ve also had some incredible wins. The team I’ve built is the most impressive, cohesive unit I have ever had the pleasure of working with. I give them the space to shine, and know they’re going to be honest when we chat, because I’m honest with them.

Q: Can you share a strategy that helped you succeed in roles you were initially not qualified for on paper?

As cheesy as it sounds, fake it till you make it. Often, when someone is deemed “not qualified” for a role it’s because those hiring are focusing on “qualifications” that mean nothing once you’re doing the job. I know what I’m good at, and I know I’m better at what I’m good at than most people, so I figure out how the heck I’m going to get that point across on a resume, or a cover letter, or in an interview. If you go into it already doubting yourself because you don’t have a degree, or you haven’t technically had the job title they need, you’ll be spending too much time trying to sell it to yourself than you do to those that you should be selling to in the first place.

Sometimes, you’re not going to get the chance to show off your skills, but if you don’t try because you’re too nervous for a stranger to not give you the time of day you’re never going to know how incredible it feels to crush it in a job on paper you had no business applying for. 

Q: As the Vice President of Customer Success, what strategies have you implemented to make the support experience the number one driver for retention in your company?

The support experience is what it is today because I have trained my team to take their time and find the actual reason why the customer could no longer continue independently. The support experience crumbles instantly when the customer feels like you don’t care enough about their success to spend time helping them. Make the customer leave the conversation feeling confident to continue on their own, but safe to ask questions if they need it. Do that and they’ll have no reason to look elsewhere.

Way too often, I experience support myself where you get sent gibberish that has nothing to do with the issue. Probably because the support team is stretched too thin and is pressured to answer more more more, regardless of what you’re actually sending out. Why? They’ll just have to answer more more more all over again when the people write back angry and confused. It’s so inefficient and it’s so unfair to the support team. 

Q: What's been the most challenging aspect of scaling SaaS support teams, and how did you overcome it?

I don’t think this is specific to SaaS, but it was hard to not have the time to be as hands on as I was in the beginning. As the business grows, the information you’re gathering grows and the opportunity to explore what you’re learning grows. And the chance to actually tackle what you’re learning to make your team and the customer more efficient grows. It’s incredible! But, it’s also time consuming. 

Working remote, especially, you can’t be alone in your tower. You need to build the team you need to deliver the results you require, but you also need to build the team you need to collaborate and work with, so finding the balance, especially early on, was a struggle. I burnt out trying to do it all. Once I started to delegate, but in a way that felt inclusive, I was, and still am, blown away at how efficiently we operate, and how connected I still feel to everyone. 

The other day I was looking at ticket volume from February 2023 and February 2024 and our volume had reduced by more than half. But our business has grown! That’s a success I want to celebrate.

Q: How do you keep the harmony between boss mode, family fun, and me-time? 

Oof…Harmony is aspirational…think that’s the best way to put it. I’ve accepted that I’m in a season of life where harmony is beautiful when it happens, but it’s usually not in the cards, and that’s okay. Just last night, I was having a moment. All of these incredible and unexpected things are happening, but yet I was so mad at myself because I wasn’t as present as I felt like I needed to be in that moment with my kids. I’m lucky that I have a true partner in my husband who tells me, like he did yesterday, that I can’t be an overachiever in every aspect of my life at all times. And in that moment, I needed to give myself some grace. 

That being said, it all comes in waves. No one can “have it all” without making some adjustments to what having it all actually means. I’m grateful for this life we’re building with our boys, and this career that allows me to stay true to who I am and help others be successful. I’m also grateful for the moments I take for myself, I’ve got a half-marathon to train for, I’ve taken up quilting and I’ve been working on some interior design projects. I think back on my journey and what I’ve achieved and it’s pretty nuts. Me 15 years ago would never have dreamed that I would be in a place where I’m building international support teams, and developing a space for people to approach leadership with kindness, and make positive change for themselves and others. And as a mom, I love that I’m showing my boys that success can be bumpy and challenging, but fulfilling and exciting. It’s a ride I’m glad to be on.

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