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OpenSpace’s Shirin Oshidari on the Evolution of Sales

By Jennifer Toton

January 23, 2023

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Recently, my colleague Shirin Oshidari, our VP of Sales, sat down with Tracy Young, Co-founder of TigerEye—and Cofounder and former CEO of PlanGrid—to share insights from her career in the construction industry. The interview appeared in the inaugural issue of Tracy’s new newsletter, Predictable Growth, a monthly Q&A with top women generating revenue for their businesses. Tracy launched her newsletter to reach and support frontline saleswomen navigating their careers.

Shirin has sold to a variety of customers over her 30-plus-year career, including construction workers and rocket scientists. In her current role at OpenSpace, she is responsible for sales and business development across all market segments.

Their fascinating conversation follows below.

Tracy Young: What’s something you believed early in your career that you now think is wrong?

Shirin Oshidari: I was raised with this Persian saying: “Perfume smells by itself, you don’t need to advertise its aroma.” However, in today’s society believing in this saying doesn’t get you far. As my son’s middle school teacher told me, self-advocacy is key. I still struggle with this mindset, since it seems to contradict the cultural value of humility that I was brought up with. But I have come to terms with it and try to keep a good balance. I used to overachieve and make President’s Club year over year but not get promoted. It took me a while to understand that just over-performing doesn’t give you a promotion; you also need to network and make sure that everyone knows about your accomplishments.

Tracy Young: Sales has a reputation of being a boys’ club. Is that still true today, or are sales teams evolving to become more gender-inclusive?

Shirin Oshidari: Sales is still male-dominated. The issue is twofold: (1) Women are shying away from entering this line of business given the optics, and (2) there are significantly more male candidates (often with direct experience in the field) for many open positions, and that makes it harder for women to get in.

That said, women can succeed. I’ve been in this industry for 30+ years, and I remain optimistic that sales is evolving. It requires a lot of stamina, grit, and hard work. There are quarters that you may not end up on top, but you keep at it and figure out what went wrong, and try again. Never give up—where there’s a will, there’s a way.

I believe sales teams need to evolve to become more gender-inclusive. Diversity in business benefits the bottom line. With diversity, you get more innovation and thinking outside of the box. I am doing my best to hire not only as many women on my team as possible but also individuals representing other diverse backgrounds. Like everything else, women have to help each other and themselves to enter the field and start changing the landscape.

Tracy Young: What skills are necessary at the VP of Sales/CRO level to work and perform under so much pressure?

Shirin Oshidari: These are some of the skills that I believe are essential for a VP of Sales/CRO: leadership, coaching, emotional intelligence, collaboration, negotiation, building strong networks, identifying talent, and recruiting great sales managers (and redeploying team members that are unable to meet expectations).

The sales leadership team is the most important thing that a VP of Sales must get right. These are the leaders that will set a positive example and help coach the rest of the team they directly manage. I believe in hiring team players who work well together, have each other’s backs, and support one another. You can’t build a company with one or two heroes; everyone needs to pitch in and contribute to the greater goal. Once you have the right team in place, then you need to make sure that you come up with the right goals—not too high that no one can achieve them, but also not so low that they’re a slam dunk. Then it’s all about coaching and training the team to get to the top of their game(s).

Tracy Young: How do you recruit the best available sales talent, and what behaviors do you incentivize?

Shirin Oshidari: Recruiting and hiring the right talent is my number one job, and I am always looking for good people. I am fortunate that I have worked with a lot of talented people during my career, and I can leverage that awesome network.

The behaviors I look for include having a positive attitude and humility; being a self-directed, active learner and team player; being willing to share their best practices, so the whole team gets better; and taking responsibility for their actions and results.

To ensure we hire the right people, we do a thorough interview and background check. We also have our candidates do a mock presentation to a panel and role-play a sales situation. It’s best to see the candidate in action instead of simply listening to them talking about themselves.

Tracy Young: How did you get into sales?

Shirin Oshidari: I studied computer science in college. When I finished school, the only place that you could find a programming job was in Silicon Valley, but I was young and liked the excitement of San Francisco. I asked around to see what kind of jobs were available in the city—everyone said that only marketing and sales positions were available, but I had no background in those areas. However, after looking around for a few weeks, I got hooked up with Kelar Corporation (Primavera Systems Reseller) through a family friend. Though I originally applied for a programming job, I decided to help them get started by taking a sales position…and I loved it. I loved meeting different customers, talking about their challenges, and helping them become more efficient and win more projects. I enjoyed the overall challenges that come with sales. I sold, trained, consulted—I did it all.

Back then, I was the only saleswoman selling to construction folks. Most assumed that I didn’t know anything about construction, but I quickly proved them wrong. I was the exact opposite of what you would expect on a jobsite—I am a 5-foot-4 Iranian woman that walked onto jobsites in high heels. The only thing that I had in common with them was that I also drove a truck. I dealt with a lot of racism and sexism, but I kept closing deals. I didn’t take anything personally, and I used it as fuel to keep going.
I sold to construction workers, manufacturers, and even rocket scientists. Rocket scientists may know a lot, but I knew my software products inside and out and how they could help prospective customers. It gave me confidence early in my career that I could sell to anyone.

Subscribe to Tracy’s newsletter to receive more great content in your inbox each month and reach out to her if you’d like to be featured in an upcoming interview. And be sure to visit our Careers page, as we are always on the lookout for great people.

A version of this content originally appeared in the Predictable Growth newsletter on LinkedIn.

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