How I Meet 500+ Customers A Year As A CEO
Everyone has parts of their job that they love and parts that they loathe. The parts that energize you and the parts that drain you. As you grow in your career, you’ll also grow deeper in understanding which activities are doing what.
My tank is refueled by interacting with people. My favorite part of the job of running Gainsight is the diversity of people with whom I get to interact across all our stakeholders—teammates, their families, clients, partners, investors, and even folks in our community. Yes, I am definitely an “E” in Meyers-Briggs language.
So when I saw a recent HBR paper that said the typical CEO spends 5.6% of their time with clients, I was shocked. In fact, I was so surprised that we asked an intern to look at my calendar and determine what my percentage is. Turns out for me it was 17%.
That averages out to roughly 11 clients a week, 45 clients a month, and over 500 client meetings a year. If you are a leader looking to meet more clients, this article is for you! If you’re looking at it and imagining how draining it would be, you’re probably figuring out whether you’re an introvert or an extrovert.
I love meeting with people, and especially clients. But even for me, it takes a process to make it work. Logistically, operationally, emotionally—it doesn’t happen by accident. So I’ve broken down the mechanisms I use to try to meet as many clients as my schedule allows.
Note that we run a “high touch” business (with our average client paying us more than six figures of Annual Recurring Revenue (ARR) per year), so this process may not apply to you. But even if your clients are smaller in spend, there may be a way to scale this down.
1. Meeting our prospective clients
I relish the chance to meet companies considering a Gainsight purchase. It gives me a chance to learn what the market is thinking, allows me to help set expectations with clients before they buy, and enables me to help our Sales team in a small way.
To make this happen, I have our Sales team identify client execs for me to reach out to. We have a standard email that my assistant prepares in a draft for me in Gmail and then I personalize the message before sending.
2. Meeting stakeholders at our existing clients
But aligning with execs at your clients shouldn’t stop at the sales process. Sadly, many companies talk about “executive sponsor programs,” but very few operationalize them. If you have “exec sponsors” on your top accounts, when was the last time the exec-to-exec connection happened for each account? Are you confident that you are “covered?”
At Gainsight, we use our Stakeholder Alignment Element in the Gainsight product to ensure that this process happens consistently. When we close a new deal, we identify the exec sponsor on the relationship. If it’s me, here’s what happens:
- The Customer Success Manager for the client will get a Stakeholder Alignment notification (“Call to Action” in Gainsight lingo) on a regular basis depending on the size of the customer (e.g., quarterly for our Enterprise clients).
- They’ll get a sample email to send to me with a recommended “check in” message for me to send to the client exec and with some background for me.
- My assistant, for convenience, places the message in my email drafts.
- I can then personalize and send out.
- If I end up having a call with the client, I post my notes to our Timeline (or simply BCC the email to the client to Timeline).
3. Meeting clients based upon survey feedback
As with most companies, Gainsight receives no shortage of feedback. We use Gainsight’s NPS survey module to survey our client executives twice a year. When the response comes in, we auto-post it to a Slack channel. Since I’m kind of obsessed, I read every response.
If I see a “promoter” (very happy) response from someone I know, I drop them an email of thanks. If I see a “detractor” (lower score), I drop them a note of thanks and sometimes ask for a quick call to learn more.
4. Meeting clients based upon online reviews
Sometimes, I’ll even post my response to a review, thanking the client for the feedback.
In other cases, if the client identified herself, I will sometimes email them to hear a more detailed account or to thank them personally.
5. Meeting our prospective and existing clients when I’m in a city
I’m a nut about efficiency. Nothing makes me happier than using every minute I have productively. I thought I was just a weirdo, but turns out, there are thousands of us!
But given this schedule kick, I enjoy making sure that the business trips, as painful as the redeye flights are, are full of business meetings.
When I go to a city (say New York), we do the following:
- My Chief of Staff uses Gainsight to pull a list of clients in the city and filters (1) ones that are healthy (where we could possibly get them to be an advocate or expansion) and (2) ones that need help.
- We will review the list with our Client Outcomes (Customer Success) team to make sure they agree with the targeted contacts.
- Similarly, our Sales team pulls a list of prospective clients to meet.
- My assistant drafts emails (which I personalize) from me to each potential meeting.
- Again, after the meetings, I post our notes to our Timeline.
I’ve found this approach of a direct outreach from the CEO is more effective than trying to have the meetings organized by my team.
Of note, my personal record was 10 in-person client meetings in one day in Manhattan. I’m particularly proud of that, given the number of Ubers, lobby sign-ins, and slow elevators I had to deal with!
6. Meeting clients in our advisory boards
Like most companies, we’ve identified a list of our top strategic clients for our advisory boards. I use the term as a plural, since we realized we need multiple boards as we grow. We have one Strategic Advisory Board (SAB) that helps guide the company overall. We have separate boards to advise us on new product (e.g., our Product Experience product), on our technology (e.g., for our Gainsight administrators at our clients) and on our delivery (e.g., for our Professional Services team).
For our SABs, we decided to host them in person when our clients are together. I’ve found that the strategic discussions are harder to hold remotely, no matter how great the video technology is. Our top client execs typically attend our Pulse event in San Francisco and our annual CXO Summit. In addition, many of them go to TSIA’s twice-a-year events. So we pick a lunch spot during these four events to bring people together.
7. Meeting clients in monthly dinner series
To make sure I have a rhythm of feedback, one of my favorite traditions is a near-monthly dinner series that I hold for CS leaders in the San Francisco Bay Area. I have a few core rules for this:
- It’s hosted by me and one or two other Gainsters.
- We keep it small—10-12 total people.
- We always have a private room and one conversation.
- We keep it personal and vulnerable by starting with an icebreaker question (e.g., “What’s your secret superpower?”).
Logistically, we’ve made this pretty easy. My assistant keeps a list up to date of client execs in the Bay Area. She books a private room. We then email the list and tell folks that (accurately) the dinner will book up fast. Side benefit: I’ve eaten at almost every nice place in Silicon Valley.
8. Meeting clients at our company events
At Gainsight, we host a TON of events—from our annual Pulse event to CXO Summit to our Pulse World Tour to Pulse Europe—you name it, we do it.
I see the cocktail party during these events as a great opportunity to hear from clients in an ad hoc fashion. I always try to have some prepared questions to help get feedback:
- “What did you see or hear today that was the most valuable?”
- “What part of the product is driving the best outcomes for you right now?”
- “What recently released feature from Gainsight are you the most excited about?”
- “If you had a magic wand to make us do whatever you want, what part of the roadmap would you have us work on next?”
9. Meeting clients at third-party events
Similarly, I attend many third-party events, including some swanky CEO boondoggles.
We make sure we are hyper-prepared for these. My Chief of Staff and I will scour the list to identify clients and important prospective clients. If we decide to meet some, we’ll draft up emails in advance per the processes above.
And when I’m on the spot at the event, I love using our Gainsight Mobile App and our Sally Bot specifically to always be able to look up the current health, sentiment and financial relationship for a client that’s walking toward me.
10. Meeting clients during job transitions
So obviously I love meeting clients, but what I love the most about it has nothing to do with OKRs or business goals or product roadmaps—it’s connecting with them as human beings. As such, I relish the chance to talk to our clients during some of their most important and maybe even stressful times— like when they’re in transition between jobs.
I’ve spoken to hundreds of CS leaders one-on-one to help them navigate the job search process including:
- Understanding how to position themselves.
- Giving them advice on their LinkedIn profile.
- Introducing them to potential opportunities.
- Giving them a backchannel or being a sounding board to compare various paths.
- Acting as a reference for them.
In these processes, I learn so much about the true motivations of our profession—and about how brave people in this new role are.
A Challenge To Meet With More Clients
It’s the joy of my job to get to interact with people and I’m happy to have so many forums to make this happen. But if you’re closer to the industry average or even below it, I want to challenge you to try out a few more client meetings. I’m convinced that in order to be human-first, you have to deal with customers on a human level. And that means spending time with them—as much as you can. I hope this article helps you think of some ideas to meet more clients in your day-to-day work, whether you’re a CEO or not. Take a look at the session we did with SurveyMonkey at PulseCheck to get an idea for how every teammate at your company can get more client time.