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June 02, 2020
Tips and Guides

Mailchimp’s VP of Talent Strategy, Andy Pittman, on Curating Talent and Technology in Recruiting

Recruiting Mailchimp Hero

By Calendly

Mailchimp has evolved into one of the most powerful marketing platforms in the tech industry and continues to push its brand into bold new territory. Ever wondered how a company staffs for creative and technical acumen across three major cities in the US? Mailchimp’s VP of Talent Strategy, Andy Pittman, talked to Calendly about how his team recruits the very best “misfits and weirdos.”

by Andy Pittman, VP of Talent Strategy at Mailchimp

When I entered the job market, my dad gave me some good advice:

“No matter how much you’re being paid or what your title is, always find ways to add more value; that’s how you’ll become invaluable.”  

Those words have driven my career — through large organizations, small boutiques, self-employment, lay-offs, and ultimately into the technology startup world, where I found my  dream job: Vice President of Talent Strategy at Mailchimp. 

Mailchimp was built by misfits to empower underdogs everywhere. We’ve been called “a bunch of weirdos,” and that’s perfectly okay with us. My team (and the rest of the People Department) enable the organization to grow culturally, instilling values of diversity, accountability, innovation, and trust. We have the challenging task of not only finding the aforementioned misfits and weirdos, but ensuring their unique perspectives drive the culture (and the business) forward. We’re constantly fishing for new talent and simultaneously identifying new ponds to fish from. 

We engage with tens of thousands of wonderful people every year, and we’ve grown to appreciate passion and purpose more than pedigree, but we’re all too aware of the pitfalls: familiarity and loss aversion biases are very real traps in hiring, so we try to focus on behavioral interviewing practices, avoiding more traditional interview questions. You probably won’t hear anyone on my team ask a candidate, “What is your greatest weakness?”

“You probably won’t hear anyone on my team ask a candidate, ‘What is your greatest weakness?'”

If we can understand the motivations that drive work ethic and leadership qualities, we will have a better sense of how candidates will perform and influence others on their teams. The qualities we’ve found to be most successful at Mailchimp include deep focus on the customer, innovative problem solving, systematic thinking, and resilience. There are other learned behaviors, like humility and empathy, we value as well. We want our people to lift up those around them, and relate to the complexities of our customers, and by distilling a candidate’s way of thinking down to a fundamental “why,” we really get a sense of what will make them successful.

The Candidate’s “Why”

In every interview I participate in, I try to understand the person’s “why”. Why are they here today? Why do they do what they do? The best answers I hear are genuine, less about short-term benefits, and more about long-term impact and story creation. I look for authenticity, not perfect answers. For example, I love when a candidate has a firm grasp on the learning goals they have for themselves, as well as the long-term impact they can have on their friends and family, their field, and the market they serve. What story do they want to tell at the end of their career or simply, at a holiday party? They then have a vision for how this role at Mailchimp aligns with their career aspirations and how our culture and values align with their own; that’s a fun conversation to have. 

Technology in Recruiting 

I’ve had more of those fun conversations than I can count and watched Mailchimp grow from a few thousand applicants a year to almost a hundred thousand. The importance of technology has become critical in providing a thoughtful and ironically, human, candidate experience. 

“Scheduling is a task perfect for automation, and Calendly is a tool proven to make the lives of any recruiter, coordinator, or manager much easier … With tools like Calendly, Mailchimp is provided the space and opportunity to let our culture and values shine through. “

Scheduling is a task perfect for automation, and Calendly is a tool proven to make the lives of any recruiter, coordinator, or manager easier. Without all of the back-and-forth of scheduling interviews, teams become more efficient, allowing for clear assessments of candidates’ competence throughout the interviewing process. With tools like Calendly, Mailchimp is provided the space and opportunity to let our culture and values shine through.

A Few Ways Scheduling Tools Improve Recruiting

  • Many companies use Calendly’s as candidates schedule their phone screening, allowing them to ask questions they’d like to get answered during the process.

  • Because many companies source talent from around the world, they rely on video conferencing to understand how they might communicate with a team in-person.

  • Every interview process is unique, and sometimes you might need to pull different team members into an interview. Calendly offers that allow you to send scheduling links with different combinations of team members.

“Whatever the benefit, we only use tools to improve the efficiency and effectiveness of our hiring practices; they should never introduce additional biases into the system …”

Whatever the benefit, we only use tools to improve the efficiency and effectiveness of our hiring practices; they should never introduce additional biases into the system, but any organization dealing with a high volume of applications, or even a lean staff, can benefit from automation. We all know the seemingly mundane tasks of our day-to-day, like scheduling interviews, can create a significant backlog if we don’t scale the process. No one wants a negative candidate experience. 

The future will undoubtedly see innovation in technology, and hopefully, that technology will enhance the humanity of our jobs.

Mailchimp has more than 1,000 humans working to enhance the customer experience, and we continue to grow, expanding into the global market and innovating our product faster and with more creativity than we ever have before.

Talent Acquisition continues to put both candidate experience and hiring manager experience on a crowded pedestal, but we have to continue to seek creative ways to tinker with our operating model and ensure the Mailchimp hiring experience stays effective. We love technology and the convenience it affords us, but we love people more. Finding humble, creative, and independent thinkers makes every day at Mailchimp a great adventure, an adventure I’m humbled to be a part of. 


As VP of Talent Strategy at Mailchimp, Andy Pittman and his team focus on ensuring Mailchimp grows with a diverse group of humble, creative, and independent thinkers who are passionate about empowering the underdog. He oversees all recruiting and talent acquisition, people development opportunities like apprenticeships and internships, and learning and development initiatives like Mailchimp University, an MBA-style program taught by Emory University professors. Prior to joining Mailchimp, Andy built out the talent function at Pindrop, and helped build Scoutmob by running talent and managing sales and company operations. Andy graduated from Auburn University and also founded an Atlanta-based holiday decorating business and Big Gorilla Jerky.

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