“Strong women leaders.” With Jason Hartman & Jessica Day

Don’t be a sales-first organization. It costs substantially less to keep a customer than it does to find and sign a new one. In the early days, we banged a gong every time we got a new customer, but now, we’re even more passionate about our renewals. If you keep hunting for new customers, but […]

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Don’t be a sales-first organization. It costs substantially less to keep a customer than it does to find and sign a new one. In the early days, we banged a gong every time we got a new customer, but now, we’re even more passionate about our renewals. If you keep hunting for new customers, but don’t figure out why others don’t stick with you, you’ll never grow.

As a part of our series about strong women leaders, I had the pleasure of interviewing Jessica Day.

Jessica Day is Co-Founder and Chief Marketing Officer at IdeaScale — leading idea management software for the enterprise and government. IdeaScale has a client roster that includes numerous industry leaders, such as the Cleveland Cavaliers, Doctors Without Borders, Freddie Mac, Marriott Vacations Worldwide, NASA, the United Way, the US Air Force, and many others. Day volunteers for sustainability organizations and lives in Napa, CA. She holds a MFA in English, Creative Writing from the University of Washington.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

Igrew up with a passion for writing and stories — I was one of those kids that (if you sat next to them on a field trip) would assault you with a stream of questions to get to know you better. Then — unbeknowst to you — I’d put those details in some short story that I was writing. As I completed my Masters in Creative Writing, I found that the digital age had brought with it a need for continuous content creation and I started writing for a number of different companies: Microsoft, Ascentium, while also freelancing for several smaller firms which is what led me to my co-founders and our company, IdeaScale.

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

I think one of my favorite, silly start-up moments was when we had finally gotten our first real office that was just us on the ground floor of this old warehouse space and my Co-Founder and CEO, Rob Hoehn was on his way out to deliver some signed documents. So he got on our electric office scooter, drove it once around the office through our desks and zoomed out the door shouting “we’ve got a start-up!”

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?

This was in one of my first jobs out of college; I’ll never forget turning to my manager who had just hired me to work on sales enablement and asking her what she meant when she said “RFP” (Request for Proposal, by the way — a sort of application that you fill out to pitch your business). I was so embarrassed to ask that question, because it turned out to be so intrinsic to my job, but my manager at the time didn’t bat an eye or shame me or gasp in horror. She answered the question and told me to keep asking more so that I could learn. I have always wanted to be a leader like that ever since.

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?

I can’t say enough how grateful I am to my co-founders: Rob Hoehn, Josh Folk, and Vivek Bhaskaran. I don’t think I could ask for a better support system or set of advocates. I deal with “imposter syndrome,” like many other female founders, and they are so great at encouraging me to own that I am someone who is part of building this company, not someone who just works here. I’ve always felt comfortable saying “I don’t know how to do this, do you have any ideas?” They have also pushed me to be the one

that speaks at events or publish on behalf of the company which is working to increase my own confidence level and spreading the message that women can talk about tech companies.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I’ve read that there are VCs nowadays who won’t invest in a company unless the CEO meditates. Although that strikes me as an extreme criterion — I understand the sentiment. Making space to breathe and be present is crucial. I also can’t overstate the benefits of exercising (which everyone already knows about) and karaoke (which surprises some people). I have secretly prepared for a big presentation by singing “What’s Going On” in my car before walking into a building.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I work in the innovation space and there have been numerous studies published about the benefits of diversity and inclusion on innovation programs. The stat I quote most frequently? Companies that report high levels of diversity are 45% more likely to report that their firm’s market share grew over the previous year and 70% more likely to report that the firm captured a new market.

But apart from the financial and organizational benefits, leaning into diversity and inclusion just makes us better people. That level of self-reflection is what helps us overcome our blind spots, get surprised, and find new joys. At IdeaScale, we have a strong commitment to improving our own diversity initiatives, but I don’t see that journey as ever having an end point. It is just about ongoing discovery and improvement.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

I think the most important thing is to make space for discussion and action. This is one of the biggest things that we did in the wake of George Floyd’s death. We are so caught up in the day-to-day running of our business (emails that need to be answered, customers that must be serviced, blogs to be written) that making time to respond to injustice feels inconvenient or impossible. After George Floyd’s death, we decided to give everyone a week off at our company to focus on this issue. Some chose to spend that time in reflection on their own or with their families, but others did research, joined local groups, started new initiatives in our company and beyond. I think the most important thing we can do there is to continue to make space for our employees now that that week is over. Clear your plates and focus your attention on important issues.

The second and perhaps most important is to find ways to bridge the opportunity divide. Invest in recruiting diverse talent, but also seed the talent pool by creating opportunities for up-and-coming leaders. During our week of action, one of our employees decided to create a scholarship-internship program to help give more newcomers to tech some industry experience. We’re very proud of Chrystal for spearheading that project.

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 CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

I’m not sure it’s different from other leaders, but I think the challenge and responsibility is to remain curious. I find I have to constantly be looking for new inputs and data sets — even looking at old data sets or old ideas and trying to re-imagine them without the baggage of previous experience. If you don’t remain curious, there’s no way that you can have a vision for the future and that’s ultimately the most important role of leadership at an organization.

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

I think some people believe that an executive means that your “vision” is a fixed point. IdeaScale’s goal has shifted over the years from crowdsourcing ideas to innovation. And I don’t think there’s any harm in changing. In fact, I think the real harm would be if we still thought that everything was just about crowdsourcing ideas and we had never shifted from that point.

I’d also like to dispel the myth that being an executive means that you’re inherently wealthy or successful. In fact, for many of us at start-ups, being an executive is a sign of a willingness to work hard and take a risk and hope that it turns into wealth or success… someday.

Also, at a bootstrapped startup like IdeaSale, all of our money and success totally hinges on making our customers happy… and in that way… being an executive doesn’t mean that you don’t have a boss. It means that you’ve got hundreds of bosses that you’ve got to scalably make happy.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

I find it difficult to apply my personal challenges to the rest of my female counterparts. I struggle most with confidence and speaking up in a decision space, but I know plenty of female executives who excel in this category and certainly there are some male executives who feel this way, too. I find the best way to overcome this particular challenge is simply practice. Speak up when you’re most daunted — test out your voice even if you’re not sure you’re right. Making space for dissenting opinion can be a powerful ally in growing a company… or just growing yourself.

What is the most striking difference between your actual job and how you thought the job would be?

Meetings. I thought that as an executive I would have all this white space in my career to research, dream, and vision for the company. The fact of the matter is that you spend a great deal of time in meetings and discussions with others about decisions that need to be made. To cope with that, I find myself returning to this best practice that Bill Gates espoused. Whenever he was in any meeting, he was only present in that meeting — not the one he just left, not the one later that day. That is the only way he was able to have meaningful discussion… by being present.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I think that the best executives are listeners first and deciders second. Lots of people pay attention to the person in the room who says “we’re going to do this” and points boldly at some chart or plan, but I’ve always been humbled by leaders who listen and take the suggestions of others. This builds culture, faith, and also means that there are more opportunities for success, because you allow more ideas into the room.

What advice would you give to other women leaders to help their team to thrive?

Efficiency is your best friend. Find ways to save everyone thirty minutes and don’t try and fill that extra thirty minutes… just give people some space to breathe. In the age of automation, this is not only possible, but also a huge win. For example, at IdeaScale, when we optimized our Slack integration to start posting customer updates, that made our team faster, but also smarter and more collaborative.

How have you used your success to make the world a better place?

One day, my co-founder and I were talking about the issue of climate change and we looked at one another and said “should we quit this start-up and go try and work on climate change instead?” And we ultimately decided not to, because we think there’s a lot of value in showing that you can be a profitable, sustainable business and still do the right thing. We’ve tried to commit to numerous initiatives beyond our own carbon neutrality, like signing the path for progress challenge, launching a diversity scholarship, offering time off for voting, increasing our corporate giving and more. I really think you can take any business and make it a values-based business.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

Don’t be a sales-first organization. It costs substantially less to keep a customer than it does to find and sign a new one. In the early days, we banged a gong every time we got a new customer, but now, we’re even more passionate about our renewals. If you keep hunting for new customers, but don’t figure out why others don’t stick with you, you’ll never grow.

Being a first mover isn’t always an advantage. Our space is still developing even today and we moved quickly to enter the market almost a decade ago, which had several great advantages (becoming the agency of record in government, setting some of the language for the space), but there’s lots of literature out now about first mover disadvantage which is a pain point we totally feel. If I had it all to do over again, I’d love to slow down and be more methodical in those early days.

You should understand your Total Addressable Market. No matter what your exit strategy is, your total addressable market is going to play into your plan. I wish I had spent more time researching the space and developing a sense of the market before we started building a product and a team. It would’ve influenced hiring decisions, positioning, pricing, and more — all of which we figured out along the way.

Having immaculate financials will help you. One of our pet passions at IdeaScale is having a really crisp set of financials that I can reference and hand over at any time. Deciding how you’re going to track revenue, manage renewals and invoices, and get the systems to communicate is actually really powerful.

Don’t spend your money on events — put on your own event. We used to pay to go to conferences and maybe you’d find some business or maybe you wouldn’t. We found that by hosting our own global summit and connecting our customers and prospects, we found a special niche of people who became our community of practice.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

That’s so true. That you never know where an idea can lead — since ideas and innovation are inherently social things, built on connection. I suppose the movement I’m most interested in is in building a new model for profit and success — the conscious company movement.

For example, we’re actually working cooperatively with our competitors to get everyone in our industry to go carbon neutral as we have. If I could get every industry thinking about their business model beyond just their shareholder gains… I think we’d all be a lot better off.

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

Especially in the world of innovation, I believe in the quote “you must see failure as a beginning, not an end.” I have certainly found myself low or backed-into-a-corner when a bet of mine didn’t pay off… most notably when we spent several thousand dollars in the early days on a partnership that didn’t yield any results. That failure made it hard for me to shell out dollars on other opportunities for awhile, but the real opportunity was to learn from that and start looking for chances to try again and do it better. Now, we have a rich network of consultants, partners, allies and customers who help drive us forward, but treating anything that doesn’t work out as an end point for too long is definitely going to slow you down.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment 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.

I’ve always admired Elizabeth Gilbert — not just in her call to follow your passion, but in her call to all of us to stay curious. Plus, it’s always inspiring to find another female writer who speaks so lovingly about the world.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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