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Teaching Growth With Jim Conti

by Frank Kalman

Jim Conti went to school to be an educator before pivoting to the world of startups. Here he shares his insights on the transition, how startups are rethinking how they manage talent and why Chicago is a unique environment for young companies.

In 2009, Jim Conti’s days were spent presiding over a classroom of 30 energetic and curious sixth-graders. Just a few short years later, Conti would pivot into an entirely different career but one that would require just as much energy: as a talent executive in the Chicago area technology scene.

While Silicon Valley continues to earn acclaim as the capital of the world’s technology sector, Conti works at the center of a startup market in Chicago that he says is quietly becoming a sleeping giant. For roughly four years, Conti worked for technology company Sprout Social Inc., most recently as its director of talent. Conti has since moved on into a new role as people leader with another Chicago-based technology company, Dscout.

Talent Economy spoke with Conti in October 2017, when he was still with Sprout, about making the transition from teaching to leading talent, what enterprise companies can learn from startups and what makes Chicago a competitive market compared to the likes of Silicon Valley. Edited excerpts follow.

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Talent economy: You have a nontraditional background, having taught grade school previously. What did you learn teaching that’s helped with your role at Sprout?

JIM CONTI: I first look at the fact that it feels like the two are very far apart from each other. But actually, there are a lot of common concepts that translate between education and business, and hopefully they can kind of learn from each other. First and foremost, the nonprofit I came from had a focus on developing school leaders, both at the teacher level and school leader level, so principals or CEOs of school networks. With that in mind, we really pushed that development process through, thinking about a school as a business and how do you think critically about a business and develop success metrics and things like that.


• Graduated from Boston College in 2007 with a B.A. in communications.

• Joined Sprout Social in 2013 as talent manager.

• Earned an M.S. in education from Northwestern University in 2010.

• Served as director of talent at Sprout Social for two years.

• Spent early portion of career as a sixth-grade teacher in Chicago.

• Most recently hired as people leader at Chicago-based tech startup Dscout.

At A Glance

There was actually a really clear translation for me there. We were using business ideas in a school setting, so when I joined Sprout I used some of those school ideals in the business. One really good idea was the concept of classroom culture. When you’re a school teacher, you’re thinking a lot about how a classroom operates on a day-to-day basis and how you build processes and systems so that students are able to be as independent as possible and know what they’re working toward; that each of them has an individual plan that they’re actually working toward, whether that’s skill set development or emotional development. And with the translation into the company perspective, one of the things I think a lot about here at Sprout is culture, so I focused a lot on that during my teaching days, and when I came here culture has been a huge component to our success.

Specifically, developing a culture and a set of values in which our employees all feel comfortable regardless of what background they come from. That was something I think was a quick translation for me from the classroom into the business setting, because that was something that we developed in the classroom. We had 30 kids that were at all different stages of their own development, whether it was kind of social/emotional or in their skill sets and we were creating opportunities for them to succeed. So it’s not as though I’ve been teaching folks here at Sprout how to read and write type of thing, but the constructs that come in behind that definitely had some translation to the work that I’m doing here every day.

TE: Sprout is a pretty young company. What is it like recruiting and running a talent function in today’s startup environment?

“ When you’re a school teacher … you build processes and systems so that students are able to be as independent as possible. ”

CONTI: It’s funny, because with the term startup there’s no clearly defined use of that term anywhere. I have a friend that was recruiting for a 900-person company in the Bay Area, and they were constantly referring to their company as a startup, and I was kind of like, really, that’s insane to me. But I think it’s gotten to the point where the term is more about the attitude and mentality that you bring to work every day.

For us at Sprout, I’d say we’ve grown out of some of what’s considered being a startup, like will the lights be on next month? Or have we found that product-market fit yet? Both of those things I feel very confident on. The way that I would describe it today is Sprout’s trajectory is one where we know we’re going to have some sort of successful outcome; it really fits on our shoulders as a team to decide where we land at this point. It’s something that our CEO, Justyn Howard, speaks to quite a bit, that we’re kind of in charge of our own futures here at this point. We have a strong product-market fit, we have customers who love us dearly and continue to come back to us and reward us with their participation in our platform every month. And with that in mind it’s kind of our moment in time where we get to decide how successful we get to be. That’s what our team is working toward today.

That said, I think that there are a couple of things about working in talent at a company of our stage that’s interesting. First, we’re in the midst of thinking of what success is going to look like for us as a business. So we’re looking for team members who are able to balance the two worlds of us still figuring out what success is going to look like or exactly what we’re going to look like as a business as we continue to develop, but also being able to find success within that, whether that’s in kind of a microcosm of team members looking at their individual role or the role or their team, or they’re seeing the impact or role their team has on the business.

“ Things will change rapidly, and if you lose sight of what the employee experience is like … then that’s a lost opportunity to really develop trust. ”

Looking a bit more broadly at recruiting, the recruiting space is one that continues to involve. We have invested heavily in continuing to establish an employer brand. I think that’s one of the things that has really helped us in terms of a recruitment and talent retention perspective, that we are making sure that the message that we portray to candidates — whether it’s through our social channels or through our content pieces, through whatever those means are that we’re getting in front of someone — that those experiences that we talk about there are consistent with the experiences that someone has once they join the team here. I think that is something that other startups might want to key into, that things will change rapidly, and if you lose sight of what that employee experience is like, and making sure that you are consistent and honest about that employee experience, then that’s a lost opportunity to really develop trust with your team members before they walk in the door.

TE: Sprout is based in Chicago. What makes Chicago an optimal location for a startup compared to, say, Silicon Valley?

CONTI: That’s a good question, and I have to give credit first and foremost to the company founders. I was not part of the decision to stay local to Chicago, though I am very supportive of it, now that we’re firmly in the midst of being a Chicago-based company. Our CEO, Justyn, spoke recently in an article in Forbes about this decision. There are a couple of factors he and the other founders thought about when they were thinking about Chicago as the place where they really wanted to invest in and spend their time developing a business. Whether it’s from the talent pool to the quality of life here to the number of customers that we already had here, to the economic advantages of this city — all of these different factors — played into it being a really positive environment for us to build a business.

When I look at it more from my personal experience of helping to build a business in Chicago, first and foremost I’d have to say that the peer companies here in Chicago, the other software startup tech companies, I look at them as part of a community that’s really investing in the city. While we are competitive at moments with candidates or very rarely with products — but at times that pops up — we’re really looking to invest in the city of Chicago and this being a fantastic place to live and work and particularly in the lens of diversity and inclusion, seeing this community be one that really wants to focus on developing a Chicago that’s more inclusive and equitable, which I think is a pretty special take on why a business is headquartered in a certain space. I don’t know that you necessarily see that with other major metropolitan areas in quite the same way. I think that civic engagement is something that really stands out to me about the Chicago market.

The other thing that I would say here is that I’m routinely impressed with how driven employees are by having a product they believe in, having a company that they believe in. I think with what at times can seem like a sort of flash-in-the-pan environment in the Bay Area or New York, where folks are kind of jumping to the next big thing, you really see folks in Chicago investing in the business they’re a part of for opportunities to be a part of something they believe in. That really stands out in the Chicago market.

The last thing that I’ll kind of note here is that it’s been really cool to be part of an ecosystem of companies in Chicago that I think are building really quality products that are used and used well. You look at peer companies and they’re developing things that are integral to either businesses or consumers, and the way that they’re interacting with whatever that product does on a daily basis. I’m really impressed to see the integrity with which companies in the Chicago market build software products, and I’m proud to be part of that and I’m proud to be a representative of that.

TE: A lot of enterprise-level talent executives look to startups to improve their practices. What can they learn from people in your position and vice versa?

CONTI: When I try to focus on what I can parlay into lessons I’ve learned or what’s kind of the playbook for a startup, one of the things that I come to first is the fact that I am both privileged and challenged that I’ve had to build literally everything that we’ve done — or my team has; I can’t possibly take all the credit here. But with that in mind, I think that gives a lot of opportunity for experimentation and for thinking differently and critically about how something is done. For my peers that are up in the enterprise market, I think that’s what’s part of what they’re looking for or what they want to get from us a little more — is what does that experimentation look like and how do we instill that?

I know part of it comes from just being a startup and being a company that is just in the midst of figuring all these things out for the first time, so I kind of want to acknowledge that. The other one that I want to come to is around the concept of culture fit vs. culture add. Culture fit is something that is talked about pretty much in every talent conversation today. Culture is I think inarguably key to a business’ success, and being really clear on what a culture of a business is and how that business plans to continue to move forward — that’s something that I think is table stakes at this point. Still, what you do with it is still very much up in the air for you as a business.

Here at Sprout, I mentioned culture fit vs. culture add. We’re in the midst of shifting from a culture fit mindset to a culture add mindset. What I mean by that is we believe that culture is a foundation upon which folks are able to stand — not a box within which they fit. So what that means is during the recruitment process and once someone starts on the team, we want to make sure that team members are able to find different opportunities to connect to and invest in our culture that feels very personal and relevant to them, and thus creating a lot of that personal buy-in. So connect that to what I was saying about the teaching methodology of creating your classroom culture, when you’re working in a classroom of 30 students and they’re all working on different things and developing different skill sets, making sure to create a space so that regardless of where they’re at in their own process they’re still able to be a part of that community and be successful.

The other thing I’ll add from a recruiting perspective is the concept that from a culture add perspective, during the recruiting process, it creates a lot of space for us to look for folks that have different experiences, skill sets, backgrounds than what we currently have on the team. Because we know that as we continue to grow and expand as a business that those additional mindsets or mental perspectives are going to be really beneficial to us as we grow and think about building new products or as we launch in new markets. Something that I’ve seen as we’ve done some international recruitment is looking at different cultural values that are local to different employees and making sure that we’re understanding what those things are, pulling them into our community and celebrating what is unique and special about those. It helps to make us a stronger business.

For enterprise level customers or peers, the thing that I think about is whether or not they consider what that looks like for them, what they’re development process looks like, and what are their strategies and goals in terms of thinking more critically about either domestic or international expansion. But for us there’s a lot of value add for having multiple perspectives at the table to make sure that we’re thinking critically about the products that we’re building and that they’re the best products that they possibly can be.

Frank Kalman is the managing editor of Talent Economy. To comment, email