Jen Grant of Appify: 5 Things I Wish Someone Told Me Before I Became a C-Suite Executive

People will sugarcoat the details because they want to impress you. I have always thought of myself as being approachable, thoughtful, and friendly — in other words, not scary. Yet still in my first role as CEO, I realized overtime that I wasn’t getting the full story from my team. Not that they were intentionally keeping information from me, but just the mantle of “boss” was enough for them to sugarcoat the details. It wasn’t until I dug in, met with customers myself, listened into the sales conversations myself, that I really began to understand our ideal customer and how to focus the team on those buyers.

As part of our series called “5 Things I Wish Someone Told Me Before I Began Leading My Company” I had the pleasure of interviewing Jen Grant.

Jen Grant has spent the last 15 years building companies from the ground-up and taking multiple companies to over a billion-dollar valuation. As CMO, Jen Grant led Looker’s marketing until the 2.6B acquisition by Google in 2019, led the rebrand of Elastic and built the team that took the company public for 2.4B in 2018, and grew Box from a small start-up to an industry-leading enterprise content company with a 1.7B IPO in 2015. Prior to that, Grant spent 4 years at Google leading the Google Apps EDU, Gmail, and Book Search marketing teams. She holds an MBA from Wharton and a BA from Princeton.

Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Absolutely. Believe it or not, I graduated from college thinking I wanted to be an actress and ended up spending a year traveling with a children’s theater company that performed and ran workshops for elementary school children. I had decided to take this path because the previous two summers I had run the Princeton Summer Theater program along with a group of students and loved every minute of it. Very quickly, however, in my first year out of school, I realized it wasn’t the acting that I had loved, it was the combination of creativity and business that had made those summers so special. That was the insight that led me to Oracle, business school, marketing and ultimately to Google where I fell in love with what technology can do to help people and change the world. In my four years at Google I led the Google Apps EDU, Gmail and Book Search marketing teams working with amazing and passionate people. When Google got a bit larger, I joined Aaron Levie at Box when it was just 30 or so employees and grew Box from a small start-up to an industry-leading enterprise content company with a $1.7B IPO in 2015. I led the rebrand of Elastic and built the marketing team that later took the company public for $2.4B in 2018. Then as CMO, I led Looker’s marketing through its $2.6B acquisition by Google in 2019. It was at this point that I met Hari Subramanian at Appify (formerly Turbo Systems) and knew it was time for me to take the leap into the CEO seat. It was clear that we have the perfect complimentary skills — while scaling is my superpower, building amazing, scalable products is his. So, we joined up to build the next billion-dollar company. I saw the product, its platform and extensibility, and met some of the customers who are championing the product already, and it was clear that this was the company for me.

Can you share the most interesting story that happened to you since you started your career?

I would say my first month at Appify was the craziest, as I came onboard as a first-time CEO in March 2020 right as a global pandemic hit. Within my first 30 days as CEO, I had to shift the entire company to operate virtually, onboard from my house, and meet and create relationships with my team without ever actually meeting many of them in-person. I also needed to continue meeting with VCs virtually to secure additional fundraising in a completely different landscape, while at the same time having all four of my kids and my husband at home with me. Zoom is a funny thing because you can only see what is behind a person, you can’t see what is happening all around them. During those early months, I remember pitching the partnership at Mayfield, at the time, probably the most important pitch I would be making. I was standing in a small corner of the room where the light was better, my laptop balanced on a stack of boxes, and one of my daughters, at least twice, came up and tried to ask me a question about whether she could go outside. All while I was presenting and convincing them of the huge potential of Appify.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

“Tell me more” — Early in my career I was quick to jump in and share my opinion. I didn’t listen enough and didn’t look to find connections. I had a great mentor at the time as well as a great leadership coach that helped me realize I needed to slow down and understand the other person’s point of view. When someone says something, you disagree with, ask them to “tell me more” and look for the gold — the thing they say that you CAN agree with. More often than not, you realize that you do actually agree with some of what they are saying and finding that point of connection is all you need to collaborate and move forward together.

Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?

Leaders Eat Last By Simon Sinek — I think I’d always instinctively wanted to create a work culture that was safe, but I never really understood the importance, all the way down to the physical health importance, until I read Leaders Eat Last. People are not just happier and more productive in a company where it is safe to take risks, we are all literally healthier. At every company I’ve been at, I have tried to introduce and nurture a culture of safety so that people will take risks and not be frightened of losing their job. At Box, I helped write the company values, one of which was “Take risks, fail fast, GSD” and then later at Looker we had the value of “Do“ which was again all about working in a safe environment where risk-taking was encouraged. It is better to move forward and get something done, then over analyze, worry, and never move forward.

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

Appify is taking a platform-first approach to modernizing enterprise software. For decades, software has been built to try to address the different needs of a company, but nothing has been built that truly addresses the needs of every business. There is always customization required, professional services to pay for and additional integrations, and business people feel reliant on IT to make their software unique to their needs. Appify makes it easy for anyone to build enterprise-class apps for their business — not in 9 months, but in just a week. TataMD turned to Appify for a quick and effective solution to deliver rapid COVID-19 testing, something only a no-code platform could possibly provide. Appify was able to deliver five apps in just five weeks. This is the power of no-code platforms in action. Just a few years ago, it would have taken months and hundreds of developers to produce even one app with the robust capabilities and functionality of our Appify apps.

The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?

Everything takes work and time. I’ve had many friends that jumped out of college thinking they were ready to lead companies. That might happen, but it’s not common. Most of us have to work, learn, work some more, and it’s not always the perfect job from the perfect employer. Sometimes you have to just dig in, get the job done, and learn. The opportunities will come, but if you’re too busy being picky, you’ll miss the best ones. I found my best opportunities by just being open to learning more, not judging too quickly, and then following my instinct on the people I wanted to work with. Early in my career, I had a great interview, but the big company then had a hiring freeze. I reached out to the person with which I had a great interview to ask for feedback and instead he offered me a role at a different company (he was leaving to join a new company). I didn’t spend a lot of time researching, thinking, analyzing; I just jumped in both feet. I knew I was working for a good person and that was enough. That’s happened a number of times in my career. Focus on the people you are working for and with. Then just jump in and do great work.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I have gotten a lot of bad advice in my career so it’s hard to pull it a part into one example. I’ve been told not to talk so much, not to be so abrasive, that I shouldn’t joke or laugh when I’m presenting to a Board, that I need to be better at “showing I understand the numbers” — all of it very much associated with me being a woman in a leadership position. Did I ignore all of it? Probably not. I still get nervous when I am talking about the financials of a business — not because I don’t understand it, but because I’ve been told that math is ‘not your strength’. So I prepare, have the numbers in front of me, and often take a breath and slow down so that I don’t panic. I know what I’m doing, but it’s easy to fall into believing the feedback.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

My strength as a leader is to help people find their own strengths and nurture them. The effect of finding someone’s superpower and then seeing it flourish is exhilarating for everyone, and it is what keeps me going when work gets hard. I also think people want to work for me because I make work fun and I build teams that treat everyone with respect. We laugh at our mistakes and learn from them, and we drive toward a collective goal of which we can all feel proud.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?

It’s about thinking more broadly about the business than just your own department. As a VP of Marketing, you’re thinking about how to get more budget, more headcount, and how to support your team and share their successes accurately with the rest of the company. While those things are still true as a CMO, you also need to deeply understand the broader strategic goals of the company and participate in trade-offs between different departments. Maybe hiring more engineers is more important to the business than more budget for your digital advertising campaign. A C-level executive needs to make those types of choices and recommendations — they should be thinking like the CEO.

What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?

CEOs are not perfect. They probably have a lot of experience to draw upon, but they will not always have the right answers. Teams need to speak up and share their opinions as well. The more data points, the more information from across the organization, the better the final decision will be.

What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?

Not actually putting the focus on the team itself. I started at Appify on Feb. 25, 2020, and I never would have predicted the road ahead of me. Almost every month something new in the world was on fire–literally as well as figuratively. But the critical component of success has been to lean in to the camaraderie and fun of the team. We can’t ignore the world or our home life anymore, especially because we are working in the middle of it and the team needs to hear that it is OK to need a moment to step out and recover. Being allowed to be yourself at work ultimately releases creativity, passion and a spirit of connectedness that drives our success.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

It’s easy to underestimate the energy it requires to keep communicating the strategy of the company to your team. I remember telling one of the CEOs from a previous company that it takes at least 7 times for people to remember anything. I was pushing him to communicate more to the team about the strategy and not be afraid of repeating himself. Now that I am in the same position, I get why it’s hard. It takes a ton of energy to keep sharing the strategy in different ways — through email, company all-hands, and other formats. And there isn’t always someone there to get you excited — it’s your job to create the momentum and excitement.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.

• People will sugarcoat the details because they want to impress you. I have always thought of myself as being approachable, thoughtful, and friendly — in other words, not scary. Yet still in my first role as CEO, I realized overtime that I wasn’t getting the full story from my team. Not that they were intentionally keeping information from me, but just the mantle of “boss” was enough for them to sugarcoat the details. It wasn’t until I dug in, met with customers myself, listened into the sales conversations myself, that I really began to understand our ideal customer and how to focus the team on those buyers.
• Yep, it’s just you. Decide. When you’re a new mom, there’s always this moment when your kid throws-up on the floor and you have this instinct to look around for “mom” to come clean it up. Then it hits you: You’re the mom. The same thing happens when you’re a first-time CEO. All of the sudden you realize that there is no one to convince and no colleague to debate. You can collect more data and more opinions, but at the end of the day, you decide.
• Wait. Am I the a-hole now? After all those years of complaining about “their” decision or “their” strategy, now it’s you. Is your team going to question your decision and strategy when you’re not around. Yes they are. And as much as you wish you could do this better than “those other guys”, there is no way you can please everyone in the company with your decisions. At Appify, we made a big strategic shift at the beginning of the year to focus more exclusively on larger companies and their IT or tech-savvy operations people. I knew it was the right decision, but a few employees didn’t agree. And while I could share the stories, data, and strategy that led to this decision, there will always be some who have a different perspective.
• Everyone wants your time. Get better at saying No. Prior to being a CEO, I tried to say Yes as much as possible. Learning about other start-ups, VCs who wanted to meet, friends who had friends that needed advice; I tried to give my time with the idea that karma would deliver back that energy some day. While that may be true, once I was the CEO at Appify, I was inundated with people who wanted “to pick my brain” or “talk shop” about any number of things. And I had to start thinking carefully about my time and honestly being more protective of it. I could spend almost every hour of a week doing calls like this, so I had to be more selective and learn how to nicely say No.
• That 8 days into my stint as CEO there would be a pandemic. That would have been great to know because honestly leading a team over Zoom just sucks. At first, it was sort of fun. I could wear my bunny slippers, be comfy, have more meetings because I didn’t have to travel, see my kids more, but then, after many months, it became the worst. I miss being with people. The excitement of working together, brainstorming, whiteboard solutions, getting excited about closing a deal, helping a customer launch, all of the fun of being in a start-up is hard to replicate while we’re at home over video. How do you inspire a team? How do you develop those connections when you’re only in two-dimensions? It’s not the same. This became ridiculously clear when we all got COVID tested and met in person. There is nothing like the energy of seeing everyone in three dimensions, speaking to the team about our strategy while watching the nods and smiles, making everyone laugh with a dumb joke, and, yes, giving out a few hugs.
• (And I’m adding a sixth): Your teenagers will still think you’re lame. Nope, that CEO title will not impress them. They’ve got way too much coolness to be impressed with your stupid job, but could you please buy that $200 pair of shoes because EVERYONE is wearing them.

In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?

Hari Subramanian is the founder and now CTO of Appify. We spent months getting to know one another and talking about the opportunity for me to join as CEO before I accepted the job. Part of the reason it took so long was that both he and I felt it was very important that we were aligned on the core values and culture we want for our teams. Today at Appify, we are bold, fearless and friendly, and we deeply value diversity. We are constantly reinforcing those values in the way we treat each other and in the way we hire. I deeply believe that everyone has strengths and it is my job as a leader to help find those strengths and nurture them. What is your superpower? Let’s find it and then focus everything you have on using it.

I also think people want to work for me because I make work fun. We all spend so many hours at our jobs, no one should dread coming to work or go home tired and angry because of how they’ve been treated during the day. I build teams that treat everyone with respect. We laugh at our mistakes and learn from them, and we drive toward a collective goal of which we can all feel proud. Everyone should go home at the end of the day energized by the work that we’ve done.

You are a person of great influence. If you could start 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. :-)

So often I see my friends come home after a day at work and they are tired and burned-out. This is not how we — as humans — should spend our days. Work should be engaging, fun, and inspiring — and you should come home at the end of the day happy. Yes, sometimes there is real work involved in doing your job, it can be hard work too, but the environment we are in at work doesn’t have to be awful. People should feel supported by their peers and their managers, they should feel safe to speak up and share their ideas, and they should not have to contend with bullies and politics. I would love to create or join a movement to help everyone live happier.

How can our readers further follow you online?

You can find me via my LinkedIn and Twitter — happy to connect!

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!