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Before lunch, Anger and I are going to have a chat, and it might make Ingrid a little nervous because we haven't discussed what any of our questions will be.
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As you can see, I didn't bring any questions. If you've met me before, you know I don't plan things ahead of time. So let's do this! We’re going to introduce you through a true/false game.
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Okay, so let's start with a few statements. True or false: national cycling champion? Yes, that is true! A software developer? True. Started a company? True. Sold a company? True. TechStars mentor? True. Merge Lane mentor? True. Chair of a non-profit? Also true. Mom of twins? True!
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Is Marty our friend? True! Softer tone, overall a badass? True. There are many interesting topics we can cover today, but one that always stands out to me is the transition from a software development background into business.
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Can you tell us a little bit about your journey, from programming to deciding that the business side wasn't so hard and that you could do it? What did that look like?
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It's funny because whenever I speak at code schools or computer science departments, I make sure to tell the women in the group to be careful about being pulled into roles like project management or organizing groups, instead of staying in engineering. I've had to resist that urge in my career. I tried out being a director of engineering once, but when we started Quick Left, it was three of us all writing code.
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Eventually, I felt drawn to trying something different and chose to move into the business side. It was a bit of a relief for me because it was a conscious choice, and I was excited about it. However, I found it difficult because, without coding, I missed the sense of accomplishment I had when I was debugging or creating something.
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In my new role, I spent my days in meetings and managing emails, but I didn’t feel that sense of achievement. I learned to just make light of the situation, and when people asked what I did, I simplistically replied, 'email, meetings, and attending various events'.
00:03:10.680
When you were first starting out and it was just the three of you, was it hardest to manage clients, the team, or the business itself?
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It was definitely the clients! I actually have a funny story about this. We started out as a PHP shop and hired a developer named Ryan. Just two weeks after he started, we informed him that we were switching from PHP to Ruby, which was pretty daunting.
00:04:07.920
In the early days, we didn't really have to manage our team much; the people we hired were self-motivated. The real challenge was educating the clients about our processes. We had many decisions to make, like how we would handle client inquiries during off-hours and whether we would conduct midnight deployments. The answer for all those things was a resounding 'no’.
00:04:46.020
Back then, our focus was on properly defining ourselves and managing client expectations. When it came to team management, we initially operated as a flat organization, which was great until we reached about 20 people.
00:05:16.410
At that point, employees began to request career advancement opportunities and clarity about professional growth paths. That's when we realized we needed some structure without losing our agility.
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As we grew, we had to navigate how to implement a hierarchy that wouldn't create unnecessary bureaucracy but would still allow for growth.
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We saw that a flat organization suited certain types of employees well, but it didn't always accommodate a diverse team, and that was another aspect we had to transition into.
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As you were getting started, when was the first time you actually started getting paid? Quick Left was a services company, so when I met my two co-founders, they weren’t making anything. I helped tighten up our contracts, drawing from my experience in women's studies, where I learned the importance of recognizing and asking for one's value.
00:07:03.780
Many developers, regardless of gender, can struggle to perceive their worth, often only associating it with work done actively coding. But being involved in project planning and breaks still contribute to the overall picture. As a result, we decided to secure upfront payments from clients to maintain cash flow from day one.
00:07:52.560
This strategy enabled us to maintain a cash surplus and attract team members who left their well-paying jobs to join us, which was quite the risk.
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I understand the challenges of getting upfront payments; it can sound unrealistic, especially when dealing with larger companies that might not agree to those terms. In fact, many clients would take ages to settle invoices, making it tough for small businesses.
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Our first clients tended to be more responsive, such as angel-funded types, who understood the importance of cash flow. From that experience, we also developed a strategy: we would raise prices by about ten percent and then offer a discount for prepayment.
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This practice allowed us to balance pricing expectations while ensuring we were paid upfront.
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To transition from being 'new kids on the block' to charging premium rates, we got inspiration from industry leaders who advocated that as developers, we should not undervalue our services.
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We modeled our pricing on respected agencies we admired, which gave us confidence and direction as we established our firm.
00:11:07.290
If you're a developer looking to grow into management, you might run into challenges in the first few months. However, if you have the right attitude, you won't mess up.
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Initial mistakes often occur later on when complications arise, coupled with the hindsight judgments you might make about past leaders.
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When you initially started hiring, was there a clear vision for how large you wanted the team to grow?
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For me, one of my main priorities was ensuring we provided health insurance from day one, owing to my background as a competitive cyclist. I saw firsthand how important it was to have it in case of accidents.
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So we had this unspoken number that revolved around needing a group of five people to qualify for insurance. Thankfully, as we worked on some uplifting projects, we managed to reach that milestone.
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Working at a small agency, I realized that many common employment perks can be taken for granted. For instance, a friend from a large consultancy lamented about individual health insurance costs, which caught my attention.
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It’s fascinating how in many places, health insurance isn’t viewed as an optional perk, creating a divide in job satisfaction and personal financial security. It reminds me of how important it is to take that burden off employees.
00:14:34.450
When you were aiming to expand the team and shape the culture, was it mostly shared responsibilities, or did everyone solely focus on their own tasks?
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We did share a lot initially, but as the organization grew, I noticed some discrepancies between team members and the management concerning business contracts. This led to distractions, preventing our developers from focusing primarily on delivering value to clients.
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We experimented with transparency in various ways, whether it was sharing financials or hiring insights. However, we had to be cautious, as too much transparency without adequate understanding could distract the team from their core tasks.
00:16:21.730
As engineers focused on solving problems, we often have an innate curiosity that makes it hard to keep some aspects of business operations hidden.
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I’d like to shift gears and explore issues tied to gender and the tech industry further. In particular, do you perceive pressure as the solo woman present in tech spaces?
00:17:01.710
In the early days, we were often the only women in many tech meetups, and it did feel burdensome to represent our entire gender. However, in recent years, I've noticed a significant increase in female voices—but initially, it was nerve-wracking.
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Overall, it feels like there is much more support for women in tech these days. I've seen firsthand how attitudes have shifted, especially among younger male developers who are excited to collaborate with women.
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Nonetheless, in the late 90s and early 2000s, discussing matters of race and gender felt isolating, and even today, it's risky to broach these subjects in public forums.
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When I was a developer, I was focused on my work, and I only addressed issues after they had time to resonate in my mind. I didn’t often feel the need to vocalize these concerns back then.
00:19:07.870
Did your insights into these topics influence how you approached the early days of your company?
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Definitely. My prior experiences pushed me to consider different organizational structures beyond traditional hierarchies. I had worked in collectives and wanted to adopt a structure where collaboration and input from everyone would help our company grow.
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While I felt we maintained an effective flat structure for a while, eventually stability and hierarchy became unavoidable aspects of managing a growing and diverse workforce.
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You worked on initiatives with NCWIT—how do you view the ongoing discussions surrounding gender equality in tech?
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While many acknowledge its importance, I do sense a gap between mere discussions and taking meaningful actions. People often have good intentions but are unaware of how their actions impact gender diversity.
00:21:16.790
One example from my experience is when we observed that women were falling short during our interview rounds. We corrected our question phrasing and the overall interview dynamics to provide a supportive interviewing environment.
00:21:43.770
By creating a comfortable space during interviews rather than relying on intimidating standard questions, we not only surfaced stronger candidates but also instilled confidence in the applicants.
00:22:03.680
If you’re a developer wanting to advance into management, it might feel like a steep climb. However, you need to be proactive in seeking opportunities that align with your interests—whether that means stepping into project leadership roles or organizing team meetings.
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In my company, we had dual tracks for career advancement—technical and managerial—so employees could grow without becoming a manager if they weren’t inclined.
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Participating in project management tasks or coordinating learning sessions like 'lunch and learn' can help acquire necessary leadership skills while allowing you to assess your real interest in such roles.
00:23:19.690
On the management side, it is essential to ensure employees have a voice and clear channels of communication for discussing their workloads and feedback openly.
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This practice enables team members to disclose when they feel burned out without immediate dependency on the managers to have all the solutions, which can lead to productive conversations about solving problems.
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Coming back to our leadership roles, it’s vital to recognize that people expect managers to solve their problems, something that can be both burdensome and frustrating.
00:25:16.850
This realization can be a turning point in understanding department dynamics and the range of skills required to effectively lead.
00:25:42.760
As you decide to change your circumstances, what led you to sell Quick Left after six and a half years?
00:26:05.530
Running a consulting company can be particularly challenging, dealing with clients and managing expectations. The development landscape was shifting, and I was reaching a point where I had to assess my own capacity to navigate the changing market.
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The labor market pressure pushed salaries upwards but our billable rates had stagnated, challenging our continued growth model.
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Additionally, I was pregnant with twins, which prompted me to evaluate how I could support my family while also managing a business through difficult waters.
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After merging with a product company called Sprintly, which brought more complexities into our structure, I found I was essentially operating solo due to losing my co-founders.
00:28:33.700
During my maternity leave, I had conversations with various companies, negotiating offers while managing my time with newborns.
00:29:09.590
Eventually, I sold the company and transitioned to Cognizant, where I felt fortunate to maintain my team and continue our work while alleviating some of my earlier burdens.
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The process of selling was emotional; however, I remind myself that the journey brought considerable knowledge and experience. I can see the success through the lives we've impacted by mentoring people who have now moved to significant roles in other reputable tech companies.
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Even though I may feel as if I didn’t get the unicorn exit I initially dreamed of, I recognize that I still managed to weather challenges and keep my team engaged in exciting projects.
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To summarize, while our success characteristics may shift over time, I am thankful for the lessons learned and successes achieved.
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And as we wrap up, let me ask you again—did you learn a lot? Yes, that’s true. Over fifty people saw accelerated career growth through your leadership, right? True. Did we achieve great work for clients? True! So, I’d say we can claim success!
00:32:49.610
Thank you, Ingrid. We’re going to transition to lunch now.
