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“Deliver what you promise”, With Douglas Brown and Claire Alexander of Capterra

For me, the best part of my years in start-up land were getting to work with intellectually curious, highly self-motivated people. I’m really proud to be an alumnus of all those organizations; each of them did a great job finding “stretchy” talent. Now I reach out to those networks when I have questions, and it’s […]

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For me, the best part of my years in start-up land were getting to work with intellectually curious, highly self-motivated people. I’m really proud to be an alumnus of all those organizations; each of them did a great job finding “stretchy” talent. Now I reach out to those networks when I have questions, and it’s still fantastic to be able to learn from them. Last week, for example, we had a product and dev roundtable with a former engineer from Opower who now looks after Slack’s design system. It was great.


As a part of my series about “Lessons From Inspirational Women Leaders in Tech”, I had the pleasure of interviewing Claire Alexander. She is the Group Vice President of Capterra, a company that helps organizations around the world find the right software for their needs. She brings nearly two decades of experience in digital strategy, new product development, and go-to-market leadership across the media, clean tech, education tech and advertising tech industries. At Capterra, she oversees all day-to-day operations and leads the strategic vision for the organization. Alexander began her career at Bain & Company and is a graduate of Harvard College and the Stanford Graduate School of Business.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a story about what brought you to this specific career path?

Well, my mom was an executive with Marriott, so she’s most responsible for influencing my career path. She’d tell us about her day over dinner, and it seemed normal to hear that she was in a meeting with Mr. Marriott, or with the head of this or that. I assumed that’s what it meant for anyone to be a businessperson! That said, I did stints in government and not-for-profits during my college years, and pretty quickly figured out that I’m best suited to the pace and productivity of the for-profit sector.

The fact that I’m in Tech is really a reflection of our economy — everything is digital, or soon will be. I love making things better, and, to me, the future is about being both more digital and more humane.

Can you share the most interesting story that happened to you since you began at your company?

About six months after I started as Capterra’s GM, my boss called and asked me if I could also take on interim CMO duties across our division, which includes two other brands. Interim ended up being about 15 months, and my EA will be the first to tell you that it’s a lot easier to manage my schedule now that I’m back to just one job!

While challenging, it was a great experience. I’m proud of how the marketing team evolved during my tenure, and love that I still work closely with that talented crew.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Ha! Well, back when I first started working, I was totally new to Excel. I distinctly remember missing out on Saint Patrick’s Day because I was working late into the night, matching data from two different data tables.

The next day a friend heard my story and clued me into this great thing called a “v-lookup,” which would have solved my problem in about 30 seconds.

I learned not to spend five hours matching data when an algorithm can do it in 5 seconds — and I learned to seek help early and often.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Yeah, there’s no way to avoid hard things. I’m pretty persistent by nature, so that helps.

I was young when I became a VP, only 29, and remember how devastating it felt to lose access to senior executive mindshare as office politics changed around me.

Luckily, during this same time, I met my husband and was spending more of my day job interacting with start-ups. I started to wonder what it would be like to be in that world — I like to say I got bitten by the start-up bug. Anyway, my husband encouraged me to go for it, and I jumped.

The choice of my life partner, and the decision to leave the familiar world for adventure, set me on a winding path toward my current role.

Finding people who support your goals, and just choosing to look at disappointment and discomfort as growth opportunities, definitely makes it easier to pick yourself up when times are tough.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

No question there is way more than one! I can thank many different people who have been champions and mentors, and some of whom I only realize were helping me in retrospect.

I really appreciate when people offer me their trust and insight into a different perspective, or organizational context. That’s definitely been true for me here at Capterra, where many people are generous with information and perspective. I’m grateful for that.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Not necessarily a quote, but the two things I believe for myself professionally are “deliver what you promise” and that “people rise to expectations.”

I’m always looking for people who treat me in ways that assume I can get the job done well, and that’s what I try to do for others.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. We’d love to learn a bit about your company. What is the pain point that your company is helping to address?

Software is a ubiquitous part of modern society, and certainly central to modern business. Most people groan when they think about having to find new software, but we’re there to help!

Capterra exists to help people find the right business software for their needs as quickly as possible.

What do you think makes your company stand out? Can you share a story?

We’re the global leader for independent software reviews and research. We’ve been in business since 1999, and have an unparalleled quality assurance process for our reviews — for everything from accounting to yoga studio software.

With so many products to choose from, figuring out where to start and what to consider can be daunting for an expert, let alone a lay person.

Capterra has done the work of cataloging thousands of options so that you can sort, filter, compare and learn from the lived experience of others without spending hours hunting around Google. And you can trust that, as an independent site, we’re there to help you consider all your options.

In fact, we just launched our new Capterra Shortlist last month. For people who don’t know where to start, the Shortlist shows you all the products that are both highly rated and popular in the market for a given category, regardless of whether we have a commercial relationship with the vendors.

It’s an unbiased, independent, data-driven shortcut — you should check it out!

Are you working on any exciting new projects now? How do you think that will help people?

If you’d asked me two years ago, I would have said international expansion and localization was our primary focus. That effort is well underway, so now I’m back to focusing on our overall user experience.

Last year we did a big quant study and found that more than 70 percent of small businesses have adopted software that doesn’t meet their expectations. That number is way too high!

Today’s efforts are focused on providing more wayfinding and personalization in our site experience. I’m really excited about that.

Something else we discovered is that getting the best software for your business isn’t about your industry or demographics. What matters is your mindset around buying software and the mindset of your organization. Does your organization only make moves in response to a competitive environment? Or are you with more of a proactive, growth-oriented organization?

I’m excited because I think we will be able to help people understand their default tech adoption persona, and based on that, give them specific advice about how to get to a great software match.

Let’s zoom out a bit and talk in more broad terms. Are you currently satisfied with the status quo regarding women in Tech? What specific changes do you think are needed to change the status quo?

I’d love to be in a place where we’re not talking about women in Tech because it’s so normal that it’s a non-issue. So, no! I’m not satisfied with the status quo.

What needs to happen? Going back to “people rise to expectations,” I think it starts in utero. Our parents have expectations. Cultures have expectations. And then there are the expectations you have for yourself. I was lucky enough to be in a family with two working parents who shared parenting responsibility. My dad was the one who drove us to school and was on the PTA, which was pretty unusual for the times.

I didn’t know I’d be in Tech, but I knew it was possible to be a female executive and have a supportive family that loved you.

If I had a magic wand, I’d vote for more female role models in boardrooms and more parental leave for both sexes.

In your opinion, what are the biggest challenges faced by women in Tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

I don’t know that I have the perspective to answer that accurately.

I would imagine it has to do with expectations, your access to information flows, and any unconscious bias that might exist in how you’re evaluated.

If you are vocal and decisive as a man, I think that’s completely expected. As a woman, you’re expected to be social, nurturing and very competent. If you challenge people in meetings, it could be more jarring to them because you’re not supposed to be threatening. You might get told you’re “aggressive” instead of “assertive.” But these issues are not unique to women in tech. It’s more about being a woman with power.

What would you advise to another tech leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth or sales and “restart their engines”?

I’d start by unpacking the” why” of what has stalled, and then thinking through what you can do to improve that.

If you are experiencing high levels of churn, that’s a huge signal that there’s something that needs to be fixed and addressed. So it’s important to get to why your growth stopped. Is it the service? Because the market itself is shrinking? Because your processes or customer experiences are not what they need to be in order to compete?

Do you have any advice about how companies can create very high performing sales teams?

Number one: It always helps if your product holds water. If your product organization can articulate to your sales organization what user needs they’re solving and why they are uniquely positioned to do that, then your sales organization can focus on operational nuts and bolts, not on tap dancing.

Within sales’ direct control, there’s no substitute for great processes and benchmarking excellence. Look at the traits of the people who demonstrate excellence, see how they interact, observe their professional hygiene, if you will: who they bring into the room, how they write emails, how quickly they follow up, et cetera. And then you supersize those great processes. You look for bright spots and put scaffolding in place so you can make those traits and behaviors defaults for the rest of your organization.

In your specific industry what methods have you found to be most effective in order to find and attract the right customers? Can you share any stories or examples?

A strong value proposition. At the end of the day, the maxim “deliver what you promise” works. We’re a marketplace. We monetize by matching people in the market with software products that could be a great fit for them, and our vendors are our paying customers. We are consistently one of their top, if not their top, source for great, in-market leads. So, we help them make money. Their success speaks for itself.

Based on your experience, can you share 3 or 4 strategies to give your customers the best possible user experience and customer service?

Sure! For me, it’s actually two things.

First, don’t underestimate the importance of pagespeed and the weight of latency. We live in an impatient world and people don’t accept latency. Having a fast, accessible digital experience is foundational.

Number two is, once again, “deliver what you promise.” Be clear about what customers should expect from you, and then ensure they get it when they expect it. Ideally you enable them to personalize the way they engage with you.

In our case, while we are a website, there are some buyers who just want to talk to a human. So we have a channel for that. Some people are happy to chat over text. Some people don’t want to interact with anything, they just want to do it themselves. We can help them as well.

Basically, be clear about what customers should expect from you, deliver what was promised without wasting their time, and be thoughtful about what will make their experience even more convenient.

As you likely know, this HBR article demonstrates that studies have shown that retaining customers can be far more lucrative than finding new ones. Do you use any specific initiatives to limit customer attrition or customer churn? Can you share some of your advice from your experience about how to limit customer churn?

This subject is near and dear to my heart because the whole concept of NPS came from Bain, the consulting company that trained me right out of undergrad. I am a loyalty superfan!

As for initiatives at Capterra, the biggest loyalty initiative we have is around personalization. There are literally thousands of studies to tell you, across any industry, how much personalization can increase lifetime, customer value, decrease churn, et cetera. But how do you do that in a thoughtful, effective way? What operational infrastructure needs to be in place in order to enable personalization? That’s what we’re focused on right now.

Here is the main question of our discussion. Based on your experience and success, what are the five most important things one should know in order to create a very successful tech company? Please share a story or an example for each.

Wow — there’s a lot in that question!

Well, let’s see. Fundamentally, you’ve got to know your customer. Who exactly are you serving? What problem are you solving for them? How important is that problem to their existence? And why are you going to serve them better than any of their other substitutes are alternatives?

When I was a consultant, I worked on a case for a retailer that was trying to understand why their same store sales were down. My workstream was to understand their customer base, and we figured out that their customers had shifted toward consumer buyers. Well — the margins on fuzzy animal head pens aren’t nearly as good as the margins on toner, so here was a classic case of a business drifting toward the wrong kind of loyal customer.

It’s always fun for me to walk into one of their stores now and look at the assortment — they seem to be back to focusing on their most profitable customers.

Secondly, you need to hire the right talent who can grow over time. If you’re a successful company, you’re going to be growing pretty fast. You’ll need to hire humble, hungry people who can grow into a job three or four times bigger than what they started with in a relatively short period of time.

For me, the best part of my years in start-up land were getting to work with intellectually curious, highly self-motivated people. I’m really proud to be an alumnus of all those organizations; each of them did a great job finding “stretchy” talent. Now I reach out to those networks when I have questions, and it’s still fantastic to be able to learn from them. Last week, for example, we had a product and dev roundtable with a former engineer from Opower who now looks after Slack’s design system. It was great.

Related to hiring the right talent, you’ve got to nurture a productive culture. I’ve been in cultures where values written on the wall were aspirational goals, or only applied to a subset of people, and those can be toxic.

That’s why I put a premium on open, transparent, participatory cultures. Seeing Capterra’s stated cultural values — seek the good, do great work, be ridiculously helpful and keep on getting better — were LIVED inside the building made me want to work there.

I would also recommend instrumenting all parts of your business, not just dev ops. You cannot manage what you cannot measure. You need to be clear for yourself about what metrics need to be tracked, and that you’ve got that instrumentation at your fingertips.

My first hire as GM was a fantastic analytics person, and he has truly upleveled the potential of the business as a result. That was a game changer.

And, finally, you need to not only deliver what you promise, but be on the look-out for how you can raise people’s expectations of what you can deliver.

Check back with me in a year, and I’ll let you know how that’s going!

Wonderful. We are nearly done. Here are the final “meaty” questions of our discussion. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Mindfulness practice. Specifically, starting when you’re young. We often use the Calm app when putting my five-year-old to bed. He frequently asks us for specific sessions, and I love that he’s got favorites.

As someone who grew up pretty high-strung, the practice of tuning in to yourself and deciding where you put your attention is a super power.

I am by no means “good” at meditation, but I see how mindfulness is helping me become more compassionate — to myself, but also for other people. I think the world would be a better place if we were all motivated and operating from that space.

We are very blessed that very prominent leaders read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂

You know, the very first person that comes to mind is Christine Lagarde. She ran the IMF, and she’s at the European Central Bank now. She’s wildly influential in a male-dominated industry. A few years ago, I happened to be at an outdoor venue in the DC area and overheard her thanking her staff at their retreat. She seemed very relaxed, lively, and genuine. I’d love to hear her stories.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

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