How Pivotal's Chicago team grew from 4 to 50 in 2 years

Andreas Rekdal
by Andreas Rekdal
August 16, 2016

"Every company is a technology company."

This phrase has gone from being a provocative statement to something of a truism, but that doesn’t necessarily mean every company knows how to act like one. 

Out of its spacious offices on the Merchandise Mart’s 13th floor, Pivotal's Chicago team is teaching some of the Midwest’s biggest companies how to adapt to this digital-first world.

Founded in 1989, Pivotal is a consultancy that uses open source software and a collaborative design and development approach to help enterprises expand their in-house product development capabilities. Clients send their employees to Pivotal’s office for an extended immersive workshop where they work alongside the consultancy group’s own developers and designers to learn test-driven, lean product development by absorption.

“In enterprise we have software developers who have a lot of different talent and skills, but not all of them are modern skills,” said Pivotal Chicago Director Austin Vance (pictured right). “How do we train and bring our developers to work on these modern cloud platforms, and how do we do that quickly?”

One of Pivotal’s answers to that question is pair programming: the client’s developers are placed alongside Pivotal’s, working together in pairs on the same computer to solve a problem. In doing so, the two developers learn from — and discuss the advantages and disadvantages of — each other’s approaches along the way. In going through the program, developers and designers also receive continuous feedback and participate in retrospectives.  

Pivotal also trains startups and legacy companies alike in building and scaling product teams — and in challenging employees in order to motivate them to stick around.

Pivotal’s clients span across industries, from Southwest Airlines, Ford Motor Company and the Internal Revenue Service, to more traditional tech companies like Hulu and Groupon. But one of the Chicago team’s most notable projects to date has been Allstate’s much-touted move to the eighth floor of the Merchandise Mart. After working with the Northbrook insurer on its technology strategy, Pivotal helped Allstate design its connected car team’s new offices.

Vance said the team advised Allstate to choose Merchandise Mart for the same reason Pivotal and 1871 chose the space: to place the company at the center of a highly collaborative ecosystem and attract young techies who see a centrally located office as a must.

Headquartered in San Francisco, Pivotal chose Chicago as its first location in the Midwest because of its thriving ecosystem of Fortune 500 companies and readily available tech talent. Along with three other “pivots,” Vance moved here from Boulder, CO in January 2014 in the midst of the infamous Polar Vortex.

“I fell in love with the city right off the bat,” said Vance. “I feel like there is this amazing collaborative atmosphere inside of 1871, inside of Chicago enterprises, where everybody in the city, in the space, are looking to transform their companies in order to become more productive, stay top of market, release more relevant and productive applications faster.”

Starting off with a cluster of desks at 1871, the four-person team had grown to double digits by 2015 and moved into a separate space adjacent to 1871 2.0. Today, the team has grown to a headcount of over 50, sitting out of an expansive space next door to 1871 3.0 where they are still hiring aggressively.

“Product managers, software engineers, product designers — we’re looking for all of them,” said Vance. “It’s time for Pivotal to reinvest in Chicago and settle in a little bit, and so that’s what our goal is for the next six months here.”

Images via Sean O'Bryan / Pivotal.

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