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A Nice Bike Ride

A Nice Bike Ride

Jennifer Toole, AICP, ASLA, Founder and President of Toole Design

By Liisa Andreassen

When she was coming up through the ranks, Jennifer Toole said she became increasingly frustrated. There were no women in top positions at the firms where she worked and, moreover, the firms had no history or tradition of promoting women. Toole said she had a sense that her employers didn’t know what to do with her. Fortunately, she knew what to do. In 2003, when she was 36, she founded her own firm, Toole Design.

“I really didn’t have another choice but to start my own company,” she said. “I couldn’t succeed any other way.”

Based in Maryland, the urban design, multi-modal and greenways firm has since grown to 17 offices throughout North America that employs over 180 people. And if Toole has her way, the firm will continue to grow like it did in 2018, when both staff and revenue increased by about 30 percent. The firm has openings for as many as 30 positions across various locations and, if the firm can find the right people, it’ll make the hires.

“I want to continue to grow,” she said. “There’s a tremendous demand for what we do. I see a lot of need.”

In a tight labor market, growth won’t be easy. But Toole and her firm have an advantage. They attract people who not only like what they do, but who believe in what they do. Of the firm’s 17 offices, 16 of them are located in high-density areas that are accessible by foot, bike or public transit. Ninety percent of the firm’s employees either walk, ride, or take public transit to work each day.

Toole, as principal-in-charge, is in the middle of creating a 75-mile bike network in New Orleans, a town known for its trolley cars. The master plan is complete and now in the design phase. Toole Design is also a leader in the field of micro-mobility, which has seen explosive growth through dockless bikes and scooters, now ubiquitous in large cities across the nation.

“It’s a brand-new way of getting around, and we are at the forefront of that movement,” she said.

While Toole did not come from an entrepreneurial family – her father was a company man – she certainly considers herself to be one, as she has always been interested in the “business side of things.” And like any good entrepreneur, Toole’s goal is to create a legacy, something that can outlast her – when the time comes to do something else.

Jennifer Toole, founder and president of Toole Design

“I would love to be able to transition ownership to people who have been with us all along and who are just as passionate as I am about what we do,” she said.

A Conversation with Jennifer Toole

C+S: How far into the future are you able to reliably predict your workload and cashflow?

JT: Despite the unpredictable nature of our projects, we’ve gotten this down to a science.  If you have good project managers and a solid administrative team that moves invoices out the door quickly, then workload equals cashflow. As such, we focus a lot of attention on predicting and managing workload.  We use different tools for the short term (two-four weeks) versus the long term (six-12 months).  We know in advance when an office or a department will either be overloaded or running light on work, and we take measures to shift workload as necessary. Finally, we don’t count our chickens before they hatch.  Our workload projections are only based on solid project wins – not on “maybes.”

C+S: How much time do you spend working “in the business” rather than “on the business?”

JT: The best part about my job is that I get to do both.  The reason I’m in this business is because I have a deep conviction in the power of walkable, bikable, transit-friendly streets to transform communities.  I wouldn’t be happy if I didn’t get a chance to work “in the business” every day.  But I also really love the nuts and bolts side of running a growing company, along with all the trials and tribulations that brings.  As the company has matured, I like to think that part of my brain matured as well.

C+S: What role does your family play in your career? Are work and family separate, or is there overlap?

JT: My family is absolutely central to my ability to be a good CEO, but they aren’t involved in the day to day work.  I have been blessed with a wonderful husband and three children who have supported me in every way, from the moment we started the company.  Their support and encouragement gives me strength, especially during those times when I’m frustrated, worn out or discouraged.  Also, I think being a working mother has helped keep my job in perspective. There is only so much time in the day, and my kids demand (and deserve) a portion of it.  I’m a type A, driven person who could have easily been consumed by my job – having a family has always kept me grounded in what really matters in life.

C+S: It is often said that people leave managers, not companies. What are you doing to ensure that your line leadership are great people managers?

JT: We spend quite a bit of time working with managers to help them understand how to be good leaders, and coaching them as they work through the challenges that every manager faces: motivating staff to do great work, ensuring staff know their contributions are valued, building a culture within their office or department, dealing with difficult situations, etc.  It frankly comes down to providing the maximum amount of support you can to managers.  So far, it seems to be working – our turnover rate is low considering how competitive the market is for top talent.

C+S: What novel approaches are you bringing to recruitment, and how are your brand and differentiators performing in the talent wars?

Jennifer Toole, third from left, with staff members from Toole Design’s Portland Office on the Tilikum Bridge. Photo: Toole Design Group, LLC

JT: We aren’t into gimmicks.  We don’t own a foosball table, we don’t offer pet insurance, or have a kitchen stocked with free snacks. What we do offer is a chance to do meaningful work for a company that has a clear mission to make communities safer and healthier places to walk, bicycle and use transit.  We don’t take on projects that conflict with that mission, even if it means we would make more money.  We tend to attract people with similar values who appreciate that we stick to our principles.   

C+S: Is change management a topic regularly addressed by the leadership at your firm? If so, elaborate.

JT: Change management has been a consistent topic of discussion from the beginning. Toole Design has grown at 15-25 percent per year since we opened our doors in 2003, so change is one thing we learned to embrace.  Growth at that pace requires constant reinvestment, so early on we learned to run a lean operation and to invest in systems that anticipate growth.  Another aspect of change management is helping our staff appreciate the opportunities that come with change. We always try to help them evolve and grow along with the company.  I’m happy to say that we have a strong history of promoting from within.  We have talented people who have stepped into leadership positions as the company has grown.

C+S: How do you handle a long-term principal who is resting on his or her laurels? What effect does a low-performing, entitled principal or department head have on firm morale?

JT: Thank goodness we have not had this problem yet.  But just in case any of my long-term principals are reading this, I have a message:  don’t even THINK for a moment about resting on your laurels!

C+S: You want high utilization for profitability, but that means employees are fully loaded with assignments. How do you balance growth, utilization, new clients, and new hires?

JT: I think every company struggles with this.  I’m pretty sure we are a long way from solving it.  For us, it goes back to accomplishing our mission – we need our staff to remain focused on delivering outstanding projects that make cities better and safer places to walk, bicycle and use transit.  I find our staff are motivated more by our mission than a profit margin – and that is OK.

C+S: They say failure is a great teacher. What’s the biggest lesson you’ve had to learn the hard way?

JT: Thankfully, we have not had any big failures so far.  We’ve never closed an office or laid off employees for lack of work.  We’ve managed to avoid financial catastrophes.  Most of my lessons have been little ones – realizing I was too cautious when I should have gone for the gusto, or didn’t take quick enough action to address a brewing problem, or failed to delegate authority and let someone else have a chance to fail.

C+S: What happens to the firm if you leave tomorrow?

JT: I’m happy to say that Toole Design would be fine.  We have been careful and deliberate to set up systems to make it possible for the company to carry on, no matter what happens to me.  I am blessed with partners who are extremely smart business people, and I have no doubt that they would steer the ship on a steady course.

C+S: Diversity and inclusion is lacking. What steps are you taking to address the issue?

JT: The lack of diversity at Toole Design, and in our profession in general, worries me. A diversity of perspectives is critical to developing well-informed and creative solutions that are tailored to the communities we work for.  This is especially true for transportation, which has a well-documented history of inequitably impacting people of different incomes and backgrounds.

About a year and a half ago, Toole Design formed a Diversity and Inclusion Committee to tackle this issue head on.  This internal committee is composed of representatives from each of our offices. Over the course of about eight months, we explored what diversity means in each of the cities where we have offices.  We looked inward and asked ourselves whether we provide a truly welcoming and inclusive atmosphere to our employees regardless of their background.  We examined our own successes and failures in addressing equity in our projects.

The result was our Diversity and Inclusion Plan, which we have begun to implement.  We have our own version of the “Rooney Rule” which says we will interview at least one minority candidate for every open position.  We still hire the most qualified candidate no matter what their background is, but I’ve found we need that extra push to get diverse candidates to the table.  We hired a new Director of Diversity and Inclusion who is taking our committee to the next level.  We realize we will never truly be finished with this work, but it’s important to start the conversation and not shy away because it’s difficult.

C+S: A firm’s longevity is valuable. What are you doing to encourage your staff to stick around?

JT: Fundamentally, it’s a combination of having great projects and being a great place to work.  We stay true to our mission, and focus on performing creative, high quality work.  We are fortunate to work in one of the most exciting areas of transportation planning and design – and attract people who are passionate about what we do.  We are on the leading edge of innovation, and our staff are driving this change.

We also focus a lot of energy on maintaining a collaborative and supportive work environment.  We’re always looking for new, cost-effective ways to be a better workplace through events, staff recognition, professional development, and more.  We make it clear that we are invested in their success. By combining these ingredients, we have been fortunate to retain staff for the long haul.


Year founded: 2003

Headquarters: Silver Spring, MD

Jennifer Toole: 31 years of experience; Bachelor of Environmental Design, Landscape Architecture, North Carolina State University; American Institute of Certified Planners

No. of employees: 180

No. of office locations: 17

Expertise: Engineering, landscape architecture and urban design and planning

Mission: Creating spaces for people in motion: Their mission is to reimagine streets and transportation networks to serve every member of the community. When they put their heads together, they plan for action and turn it into reality. From Vision Zero action plans and innovative data analyses to final design and construction documentation, their engineers, designers, and planners work across disciplines to make sure that their clients can help their communities become safer and more accessible.

Fun fact: 90 percent of Toole’s staff bikes, walks or takes transit to get to and from work.

Liisa Andreassen is a freelance writer who lives in Asheville, NC. She writes on a variety of topics including architecture and engineering, business management, HR, and technology. She can be reached at landreassen@zweiggroup.com.