CS My Way #8: Exclusive Interview with Kirsten DiChiappari, VP of Customer Success at vCom Solutions
Welcome To CS My Way #8
Welcome to this exciting new space—CS My Way—where you can learn from the best in the industry and get ahead in Customer Success and beyond.
Each week, I engage in conversations with top executives — Chief Customer Officers, VP/Head of CS, founders, and CEOs. Together, we discuss how they drive success for their customers.
💡I always learn a lot from these exclusive interviews, packed with massive value, practical examples, key takeaways, and best practices from each leader.
I hope they’ll inspire you to build world-class CS organizations and accelerate your career in Customer Success and beyond.
💥I'm thrilled to bring you today my latest conversation with Kirsten DiChiappari, Vice President of Customer Success at vCom Solutions, the leading provider that helps businesses manage the cost of their IT spend from the procurement of an asset through payment and analysis.
Thank you, Kirsten, for sharing your story and insights with us on The CS Café — #1 Weekly Customer Success Newsletter!
The stage is yours!
P.S. Want to share your own story? Fill out this quick form and I’ll get back to you over email.
About You
Can you share the journey that led to your current role as VP of CS at vCom?
It was the happiest accident.
I was in the hiring process with a different company and went to Glassdoor to do some research.
Turns out they had terrible reviews and an incredibly toxic work environment, which explained why they'd declined my request to meet with the team I'd be leading. I wasn't aware that Glassdoor had job postings until that day when I found the one for my role at vCom.
Things really do work out in a multitude of ways, as I am now lucky to work for an org that has repeatedly been awarded Great Place to Work, Healthy Workforce, Top CEOs, and Best Places to Work!
“I spent more than a decade in HR working in high-tech startups, higher education, non-profits, and finance.”
I left this career after my daughter was born when a combination of poor market forces that made employers stop investing in employees collided with a strong focus on avoiding legal issues, which led to policies and procedures being driven solely by that concern.
I found two back-to-back opportunities managing companies in the wellness space.
It was a nice transition that offered me flexibility while my children were small and also landed me in the Chamber of Commerce and Business Network International (BNI), two organizations that were valuable in teaching me how smaller local businesses survived and thrived.
In my board role, I shared a lot of advice and recommendations with fellow business leaders on how to tackle online marketing and social media, eventually parlaying this hobby into a boutique agency of my own.
I taught business owners through the Chamber of Commerce, Rhode Island Economic Development Corporation, and Small Business Association, also working with local radio, TV, and newspapers to consult with their advertisers, and ultimately selling my business to a local media group.
I led their digital agency until I took an opportunity with Presslaff Interactive Revenue to build marketing and sales programs for their customers, traveling around the country to train media sales executives.
After Presslaff was acquired, I got the opportunity to go build, and then lead the Customer Success team at BlueVenn (acquired by Upland), through their own acquisition years later.
“I like to think that I started my career with employees as my customers.”
I transitioned to have businesses as my customers and now have both my team and our customers as my customers. 🙂
Client Retention Strategies
Drawing from your experience at BlueVenn, where you were responsible for retaining and expanding a significant base of SaaS customers, can you share a specific strategy or initiative that you found particularly effective in ensuring long-term client relationships?
It's not at all original, but:
“The simplest strategy is to successfully deliver the product customers bought - as expected and when expected.”
Transparent and proactive communication is critical to overcoming any potential issues.
Waffling or avoiding hard conversations is a recipe for disaster so I encourage my teams to say what needs to be said.
Customers hate being disappointed (who wouldn't), but they ultimately appreciate clarity and the opportunity to adjust plans in advance of a miss.
Beyond that, keep talking.
Remind (aka SHOW) a customer the value your solution provides – and make sure it's actually still providing that value.
Needs change and the best way to guarantee renewals is to regularly seek alignment.
I think of what we do as a 'personal trainer' model - it's not something we can do alone; it really requires customer participation (partnership) to be successful.
Operational Efficiency
Given the breadth of services vCom offers, how do you ensure seamless coordination between departments to deliver a unified customer experience?
Technology certainly plays a big part so that everyone can access the info necessary to do their jobs.
Using the right tools for the right activities is also key, there's a joke about a meeting that could have been an email, and lord knows there are plenty of emails that should have been an Instant Message (IM).
As for the human side, two things stand out to me:
Leveraging our whole company for ideas to improve how we do what we do
And cascading information to the whole organization.
Our leadership is very transparent.
They provide regular updates on our financials, our go-to-market strategy, important changes to the market, and the impact on our business.
They don't treat any department or any role as not deserving of this information, and everyone is empowered to seek clarity, challenge ideas, and recommend alternatives.
Driving Adoption and ROI
At Presslaff Interactive Revenue, you focused on training sales teams and clients on the adoption and use of innovative solutions. How do you approach the challenge of ensuring that clients not only adopt vCom's services but also realize tangible ROI from their investment?
If you can create opportunities for a customer to grow revenue, you've got their attention.
“If you can solve a problem for them, saving them time or money, and if you can do it faster or better than they could themselves, you've got their attention.”
You have to know your unique customers and what each needs – and you absolutely have to capture what they define as success in your relationship.
This benchmark should be documented and shared between both organizations and regularly measured and revised, as necessary.
This allows for the creation of an appropriate account plan built to achieve their desired ROI.
[End Of Part 1]
Here’s what we’ve covered in the 2nd part of our conversation:
Kirsten’s Metrics for Success
Industry Engagement and Thought Leadership
Personalized Customer Experiences
Adaptability and Innovation
Building Strategic Partnerships
Cross-Functional Collaboration
Measuring and Communicating Success
Balancing Business Metrics and Customer Experience
Training and Development Initiatives
Proactive Customer Engagement & Issue Resolution
Crisis Management and Resilience
Her Tech Stack and Take on AI
Her Perspective on Customer Success Layoffs
Thought Leaders She’s Following
Her Leadership Philosophy
Her Best Career Advice
And More!
Metrics for Success
What KPIs do you track daily to gauge the effectiveness of your customer success initiatives, and how do you use these metrics to drive continuous improvement?
Here’s our North Star:
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