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OODA Network Interview: Jen Hoar

This post is based on an interview with Jen Hoar, Founder of Sinclair Insight LLC, a business intelligence and due diligence venture. It is part of our series of interviews of OODA Network members. Our objective with these interviews is to provide actionable information of interest to the community, including insights that can help with your own career progression. We also really like highlighting some of the great people that make our continued research and reporting possible. For the full series see: OODA Expert Network Bio Series.

Where are you from?

Jen grew up in a family of academics in Westchester County, just north of New York City. Both her parents were professors at Fordham University.

What did you want to be when you were 16?

Jen thought she wanted to be an attorney at age 16, largely due to her recreational, though immersive, interest in the coverage of the OJ Simpson trial at the time. She became obsessed with the legal and investigative nuances of the case, and followed every aspect of the trial. Along with an earlier fascination with Unsolved Mysteries (now in a Netflix reboot!), the seed of fascination with investigative work was planted.

Where did you go when you left home as a young adult?

She applied early and was accepted to Georgetown University, and didn’t even think to apply elsewhere. She thought that was “her place,” and she was right. “Six years and six figures on Georgetown [including grad school], and it was worth every cent,” she said. While in her senior year, as an English Major, she took a journalism class, which immediately delivered the realization: reporting was the perfect career path for an English major who’s an extrovert and wants to talk to people, and learn from them, for a living.

How did you find your calling? How did it evolve?

Jen did an internship with an affiliate of NBC News in her final semester of Georgetown, and loved it. “You’ll know you have found your calling when the work energizes you, and I felt that way instantly when I worked in that internship,” she said.

After graduation, she got a job with ABC News and worked in media in the DC area for the next five years. It was an exciting industry to be in, except the DC focus on domestic politics and policy didn’t fulfill her deeper interest in international relations and business. Jen returned to her alma mater, Georgetown, and completed a Masters in international relations in the MSFS program. “Georgetown’s program was geared to finding work in the field, not towards academia. It created the perfect opportunity for a career change, but to parlay what I had done before as well,” she said.

During the MSFS program, Jen took a course called Business Operations in Emerging Markets. The class was built around Harvard Business School case studies showcasing how US and multinational companies grew their operations around the world, often in unfamiliar or intractable markets. She loved the interdisciplinary nature of the course so much that she thought, “how can I do the work described in these cases in real life?” That rhetorical question was answered by reality: Crumpton Group, a company whose work sounded like the course syllabus, was being founded and started recruiting t Georgetown. She credits her experience there with introducing her to the business intelligence and investigative industry. She said she appreciated how they empowered her to go out in the world and talk to people, just as she’d done as a reporter, to do research for clients.

Jen loves the “hustle of the business world – the excitement of teasing out truths that help companies solve problems.” For the next decade, Jen got to practice her skills working with a diverse group of clients around the world. In 2014, she founded Sinclair Insight LLC, through which she does source inquiry (human intelligence)-based work on due diligence and business intelligence matters. After four years running Sinclair Insight LLC, and a year and a half on an investigative team at Facebook, she has returned to entrepreneurial life. “I feel like I get to be a journalist-for-hire, and that’s very fulfilling,” Jen says.

“I love what I do. Business clients have a very sophisticated and diverse set of needs. I love working with them to frame the project. Then I apply functional skills to identify the best sources and ask the right questions to solicit and elicit insight,” she explained.

Tell us about the HUMINT training session with OODA on July 23rd.

Next week, Jen will lead a training session via Zoom through “I will impart useful techniques about how to make the most of any professional interaction, whether it’s with a source, a potential investor or a new client. Asking questions and listening can be more powerful than speaking and pitching,” Jen says.

“No matter what your particular professional focus is – business development, sales, corporate strategy, or just working with colleagues – it’s essential to learn about your interlocutors’ pain points and challenges,” she explained. She’ll share the framework that she uses to identify the right sources to talk to, talk to people you don’t already know, and learn from them.

Jen reassures the introverts: “You don’t have to be an extreme ‘people person’ to benefit from, and apply, these skills in a way that feels comfortable and effective for you. They can become part of your professional arsenal and they will make most professional interactions more fruitful and less stressful. Counterintuitively, you learn more and are more accessible when you make the encounter all about the other person. Less talking, more listening.”

To sign up for the training: Master the Skills of Spies…

What has surprised you most in your career?

“I’ve come to be surprised at how indispensable listening to your intuition is, including when you have a ton of information at your disposal to make a risk calculus,” Jen says. “You can research and pull data forever, but there is only so much analysis a human mind can do. At some point, you have a pretty good read on the situation, and that is borne of experience and trusting the instincts that come from that.”

What technologies and trends are you watching?

“I’m interested in how human intelligence and technical capabilities complement each other, especially in cyber investigations, and how the two can work together to address business challenges.”

And anything that keeps Matt Devost and Bob Gourley up at night. (She’s afraid to ask, but will practice the HUMINT that she preaches.)

What is your advice for (executive) decision-makers?

Jen believes it would benefit decision-makers to frame and re-frame their intelligence questions in conjunction with those collecting on the requirements, those who are out in the proverbial field. “You have to frame things in terms of natural human conversation with sources. This may affect how decision-makers think about what they’re asking,” Jen says.

Who are your thought leaders?

Jen’s said that her longtime mentors and icons, Steve Cash of (what is formerly known as) Talus Group LLC and Matt Zaklad of China Six, have been transformational in her thinking about client engagements, source work and the importance of being a consummately courteous, appreciative and enthusiastic professional.

Quick Hits:
Currently reading: Dare to Lead by Brené Brown
Favorite piece of content on OODAloop: Jen relies on Matt Devost as her personal thought leader and guru on all things cybersecurity, and a touchstone of creativity in entrepreneurship.

Chris Ward

Chris Ward

Chris Ward (Commander, U.S. Navy (Retired)) has over 30 years of experience helping the Department of Defense (DoD) solve difficult technology requirements. She has a proven track record of building, maintaining, securing and certifying technology solutions for use within DoD. She works with Industry to identify key opportunities and provides strategic guidance and support. She is a strategic analyst and cybersecurity professional who has deep expertise in improving enterprise cybersecurity.