SalesTechStar Interview with Gemma Cipriani-Espineira, Chief Customer Officer at Chili Piper

Gemma Cipriani-Espineira, Chief Customer Officer at Chili Piper chats about the importance of strong customer success fundamentals and how this is integral to overall sales processes:


Hi Gemma, welcome to this SalesTechStar chat, tell us more about your journey through the years and more about your role as Chief Customer Officer at Chili Piper?

Hello SalesTechStar and thank you for having me! I’m hoping to provide value to aspiring CS and Support leaders with my story. I can honestly say I didn’t choose the CS world — it chose me!

I started my journey to SaaS by responding to a Linkedin ad for “UNCAPPED COMMISSION, HIGH EARNING POTENTIAL.” It was an entry-level sales development role at the London office of Vocus that was trading on the NASDAQ. I was a law graduate with bills to pay, looking for a stop-gap job that would allow me to save enough money to complete my legal practitioner’s course.

I joined a competitive team and started earning quickly. The speed of progression and ability to instantly communicate with clients was a refreshing contrast to my prior legal experience. All of the skills that I thought would make me great at law transferred beautifully to attracting, winning, and retaining customers. So much so that I never looked back. I became the fastest and highest-ever promoted employee from an entry-level role, leaving as the office’s most Senior Account Director.

Read More: Knowing What Customers Need Before They Do: Why…

I was then hired by referral to scale client services at a UK-based start-up, Decibel. I hired, onboarded and managed a global customer team of 30 from the ground up. The company offered insights that helped well-known brands like LEGO, British Airways, Fidelity and Adidas improve digital experiences on their websites. My responsibilities started out as Head of Client Services, building a team of Account Managers to sell to customers which then matured to scaling teams to help customers including education and insight services. At the time, Customer Success was a novel concept, but we took the opportunity to transform our original team of Account Managers into Customer Success Managers, with a sole focus on retention over upsell/cross-sell revenue. In this transformation, our retention rates soared and I was promoted to VP of Customer Success.

The tech quickly took off, particularly in North America, which led to me throwing my hat into the ring to move stateside. After bootstrapping the business to $5m ARR we went on to raise various rounds of funding and the company eventually was acquired by Medallia for $160M. Each round of funding and steps leading toward that sale was backed by our early customers, who became life-long advocates for our products and services.

When I was headhunted by Chili Piper to scale their customer team, what attracted me most was the company’s invaluable product, incredible growth and views on progression. During my first conversation with Chili Piper’s CEO and Co-founder Nicolas Vandenberghe, I shared my commitment to getting customers, and the customer success teams who support them, a better seat at the table by becoming a Chief Customer Officer (CCO). Nicolas was less familiar with the role but offered me a clear path to progress to CCO based on performance. We partnered to establish a Center of Excellence for our Customer Success and Support teams, which delivered fast results during times of steep growth and change for the business, and I was promoted to CCO within 10 months of joining.

As Chili Piper’s first CCO, what are some immediate near-term goals and strategies you plan to focus on?

As CCO I will continue to oversee the charge to customer earned growth while managing fully distributed global teams in pre-sales, onboarding, success, and support.  Our mission is to create and retain happy active users. We’re designing teams around this mission and challenging the status quo on typical CS and Support structures.

By way of example, we’ve built a 2022 headcount to spend more time helping customers adopt our products over just managing expected ticket volumes or net retention goals. We’ve rebranded our Customer Support team for what they really are, which is a Customer Love team, who show patience, kindness and love during our customers’ times of need. We obsess over genuine, customer-driven G2 reviews and survey feedback over long-form marketing-led case studies.

In your view, how do you feel today’s B2B Chief Customer Officers need to revisit how they structure processes and their teams to drive greater brand value and customer success?

Greater brand value and customer success is earned little by little. The outcome of lots of little good things that you do to make your customers’ lives easier is strong net retention. Because the CCO role is relatively new, there is a tendency for CCOs to follow a sales approach, obsessing on the net retention before they get a chance to drive the activities and leading indicators that drive this lagging outcome.

An example would be to focus on customers renewing today over customers who need you today. A CCO should create a structure that provides the necessary air cover for their team to be there for their customers when they need them, rather than just show up when the checkbook is out. We’ve expanded our team to provide more availability to customers and created product usage triggers so we can proactively reach out to help inactive or struggling customers.

Take us through some of your preferred sales tech and other customer tools from your journey so far that have helped drive initiatives and goals?

We have two core systems of actions for the customer teams — Planhat for Customer Success Managers and Zendesk for Customer Support Engineers. This ensures consistent standards of service for all customers, across all stages of the customer journey. We integrate these systems with the aforementioned product usage data alongside tools to drive advocacy (Sendoso, G2), meet and communicate effectively (Slack, Zoom, Chili Piper) and enable the team (Gong, MaestroQA).

I’m particularly excited about our recent partnership with ProgressionApp to establish clear skills and expected outcomes so the team can take ownership of their progression.

A few thoughts on the future of customer success and B2B sales – and how revenue/sales and customer-facing teams will need to evolve to meet changing market needs?

With the rising popularity of review sites, the future of B2B sales is customer success. In order to win new customers, there is more pressure on sales reps to prove what life after the sale looks like. I expect to see more CCO roles appear in companies looking to find a partner who can deliver this to their CRO.

Some last thoughts and takeaways before we wrap up?

I hope this article will encourage aspiring CS and Support leaders to know their worth in the B2B world. It’s important to see a path to leadership in order to run through walls for your colleagues and your customers.

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Chili Piper is a complete Meeting Lifecycle Automation platform that helps replace the tedious process of emailing back and forth to schedule a meeting with 1-click scheduling.

Gemma Cipriani-Espineira is the Chief Customer Officer at Chili Piper

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