Inside Diligent Academy’s goal to educate future tech industry workers — and keep them in Baltimore

The CEO of the New York City-based, globally reaching SaaS company told Technical.ly on Wednesday evening that he lived in Charm City for about four years while his wife took a job at local financial giant T. Rowe Price. During that time, he developed an appreciation for the city’s perseverance and professional potential. He also saw an opportunity for the company he’s led since 2015.

“Baltimore had a real impact on me,” he said. “[It has] hard-working, resilient, very talented people. The same opportunities don’t exist here, maybe, as in some other larger cities. I think there’s an opportunity for us at Diligent to help create some of those opportunities and unlock the potential of a very talented workforce.”

That belief led the governance and compliance tech company to not only set up shop in Baltimore but also establish the Diligent Academy, a training program to source and upskill sales professionals from underrepresented groups that Diligent launched in partnership with the SaaS sales and customer relations training platform SV Academy this summer.

Stafford returned to Baltimore for the Wednesday reception, in a 28th-floor room at the Four Season Hotel in Harbor East, that celebrated the program’s launch and its about-22-person inaugural cohort. There, senior-level Diligent and SV Academy employees from throughout the eastern US toasted to the cohort’s success alongside such outside supporters as UpSurge Baltimore CEO Jamie McDonald and Chief Relationship and Ecosystem Officer Kory Bailey, who helped the academy’s parent entities identify potential staffers and resources for the training initiative.

Baltimore’s new Deputy Mayor for Community and Economic Development Justin Williams also attended and delivered remarks in which he praised Diligent’s choice to develop Baltimore-area talent.

“In this 21st-century economy, we’re not just competing with Columbia or DC for jobs,” he said. “We’re competing against Mumbai and Beijing for jobs, so I’m excited for this cohort here. Take advantage of the opportunity in front of you to build your skillset, get jobs in this industry. I hope you take this as an opportunity to give back to people coming up behind you.”

Members of the first Diligent Academy cohort and their program facilitators. (Courtesy photo)

SV Academy cofounder and CEO Rahim Fazal told Technical.ly in July, soon after the Diligent Academy was announced, that his organization first connected with Diligent several years ago via mutual partners at the VC firm Insight Partners. He said that Diligent hired about 10 SV Academy participants through the JumpStart program, a similar partnership that aimed to train underrepresented peoples for entry-level positions and apprenticeships at Insight Partners’ portfolio companies — including Diligent, which Insight Partners acquired in 2016 and continues to be Diligent’s main investor.

Fazal — who, like many of SV Academy’s students, does not have a four-year degree — said that he sees his organization’s partnership with Diligent in Baltimore as part of its larger goals of making tech companies more diverse, while expanding beyond the country’s biggest economic hotspots.

“There’s this question around … ‘Do you need to be in San Francisco? Do you need to be in New York?” Fazal said. “That question, in the last two-and-a-half years, has evolved from the perspective of the employer as well as the talent. [This] has opened up interest in hiring folks in different parts of the country where there’s both ready talent, but also where the economics are better.”

MarKeith Allen, Diligent SVP and managing director of mission-driven organizations, said at the Wednesday event that Diligent Academy’s curriculum is structured along three different tracks, similar to SV Academy’s JumpStart framework: sales development representatives, customer success and customer support. He noted that the cohort’s journey started around early August, depending on when they applied through SV Academy, before the Diligent-side training began on Sept. 6. Some participants, he added, will begin at Diligent as soon as November.

“We’re just teaching people skills, teaching them about software, governance, risk and compliance, teaching them about how companies operate — all the things that we do — to get an idea of what type of careers could be available to them and get their foot in the door,” he said. “Then we teach them job-specific skills, and then we’re going to move them into departments.”

Diligent and SV Academy staffers clap during speeches at a special reception for Diligent Academy’s first cohort. (Courtesy photo)

Diligent came to Baltimore, a predominantly Black and endemically segregated city, amid a wave of economic development and research projects that seek to address or reverse this centuries-long disinvestment. Diligent seemingly answered this dynamic by building a predominantly Black, brown and Baltimore-resident inaugural cohort. (One participant came from Silver Spring, closer to DC.) Those participants who spoke to Technical.ly boasted a diversity of professional and educational experiences that they hoped would inform productive futures with the company.

Keona Crouell took the service track to leverage skills she built as a case manager for the Maryland Department of Human Services. Noting that Baltimore has several STEM-focused schools, she said that she appreciated the academy’s non-terminal approach to educating future tech industry workers — and keeping them here.

“Even if the tracks we came in on aren’t where we stay, that’s not the goal,” she said. “The goal is for you to grow and learn more. We have people here that are great in the STEM backgrounds, they just need those opportunities, and they shouldn’t have to leave to get them.”