7 Sales Development Questions Answered by a Leader at GitHub

After graduating from St. Olaf College in 2008, Keshia Hohenstein, the Global Director of Sales Development at GitHub, got accepted into the Leadership Development Program at Quad/Graphics, a commercial printing company.

For the next nine months, she would do three-month rotations in different departments of the business such as manufacturing, marketing, and customer success. By the end of the program, Keshia was convinced that she wanted to pursue a career in marketing.

However, after enough of her friends, parents, and professionals in her network recommended that she at least consider a career in sales, she decided to check it out. “Whenever people would ask me what I wanted to do, I would tell them that I wanted to have plenty of autonomy, work in a group setting with a lot of camaraderie, and have healthy competition,” says Keshia. “That’s sales in a nutshell. So after my rotational program, I decided to take the plunge. I ended up loving it.”

Keshia was gracious enough to share her time with our internal flock and lead a weekly fireside chat for current students. We host different leaders each Monday in an effort to offer our students access to authentic, successful, bold industry leaders! Keshia shared insights on everything from interviewing, to becoming a badass SDR, to being a woman and person of color in sales. Read on to see what you can learn from Keshia that will help you on your career journey.

Keshia Hohenstein's Journey Into Tech Sales

Keshia went on to work in sales at Quad/Graphics for the next three years, where she fell in love with the art of selling. But she also developed an itch to work in an industry that could make a bigger impact on the business world as a whole.

Soon enough, she realized that the tech space could scratch it. However, since she didn’t have any experience working in tech, she struggled to even land an interview.

“I applied to 30 or 40 companies and was also trying to get my foot in the door at other companies, but I got auto-rejected by a bunch of them. And honestly, I don't necessarily think there was a skills gap because I had some sales experience at that point, but I just had zero tech sales experience,” says Keshia. “These companies interview tons of people who have tech sales experience, so they weren't as interested in somebody who came from a different background.”

To overcome this obstacle, Keshia decided to apply for a broader range of roles at smaller-sized companies. She knew that she only needed one company to take a chance on her and that when they did, she was going to carve a career in tech. She knew the passion was there.

In 2012, Keshia landed her first job in the tech industry as a Corporate Account Executive at ClearSlide. Seven years later, she not only rocketed up the sales ladder, landing a role where she heads up the global sales development team of over 50 SDRs in San Francisco, Amsterdam, Sydney, and Japan, but she also rocketed up the tech ladder by doing it at GitHub.

Read on for Keshia's direct answers to the five top questions asked during our fireside chat.

1. How do you ace an interview?

“After you do enough interviews, you're going to hear some of the same questions. Don't let that tire you out. I’ve interviewed somebody who had already done a bunch of interviews with our team and I felt like he had just had a super long day. It wasn’t a good interview. So always make sure to bring the energy.”

“I also try to find out what you're telling me through your actions. Within the time frame that we're interviewing, I’ll take note of what you say you do and what you actually do. That way, I can line up your resume with your actions and see if everything’s consistent.”

“Additionally, be your authentic self. You don't want to get hired into a role because you faked it because now you've got this persona to uphold. So be you and be honest with what you want out of the company. It will shine through.”

Key Takeaways: Bring the energy, make sure you can walk the walk, and be your authentic self.

2. What does the day in the life of an SDR at GitHub look like?

“It varies, but I would say you're going to slice and dice your time between following up on emails and following up on LinkedIn. We don't make as many calls anymore because emails and LinkedIn are doing great. So you gotta make sure that you’re sending out those messages.”

“We also have our SDRs sit in on their Account Executive’s calls to glean some best practices. Then, when their AE trusts them enough and believes they’re good enough to lead a call on their own, they let them take the reins. Their AEs will give them feedback after. And if that goes well, they’ll let them sit in on the entire sales cycle because they want to prepare them for their next role. It’s like having the training wheels on.”

“On the flip side of things, our SDRs are always learning about the product and the company. They have to understand the product that they’re selling. And since we have a multitude of products that have a lot of different industry use cases, there’s a ton of different personas and value props that they need to know. There’s no shortage of material to learn, so they need to take the time to study our solutions.”

Key Takeaways: Following up with prospects through email and on LinkedIn, sit in on AE’s calls and track prospects’ entire sales cycles to prepare for next role, and constantly learning about the product.

3. What does a top SDR look like in your eyes?

“I've had some SDRs get promoted lightning-fast, like I'm talking about two rounds of promotions in three months. So these things can happen quickly if you come in and learn fast. To do this, the top trait to possess is having a growth mindset, where you constantly solicit feedback. Anytime somebody gives you feedback, take it like the gift that it is.  

It takes a lot of thought and attention to give somebody solid feedback. The best gift you can give back is to implement their recommended changes and ask for more feedback after. Showcasing that you’re hungry to learn, that you want to keep pushing forward, and that you've got thick skin is huge.”

“The next best trait to possess is a strong work ethic. Sometimes, you don't want to send that extra email, but the person that does is doing what everybody else didn't want to do, kind of like Michael Jordan. You gotta make sure that you put that hard work in every day, not just in quick spurts or binges. You gotta be consistent.”

“Another top trait to possess is a sense of urgency. You can do something tomorrow or next week, but if it's going to make a big impact, why not do it now? Let's make it happen. And the stuff that's not going to make a big impact, it’s okay to leave for later. So let’s just zero in on the stuff that is making things move.”

Key Takeaways: Adopt a growth mindset where you’re constantly asking for feedback, develop a strong work ethic, and have a sense of urgency.

4. What are some of your tips for giving elevator pitches?

“Tailor your responses. For me, if I look at a company and see that they’re hiring a bunch of app security people, I'm going to talk to them about advanced security and how we make it easier and faster. Or if I see that they’re hiring a bunch of engineers, I’m going to ask if they need help onboarding -- fast -- and if they want them to be good from day one.”

“At GitHub, a lot of people have heard of us in the open source community, so they’ll ask us why they would ever use us for their huge company projects when they’ve only used us for their side projects. It seems risky. But that’s where we re-educate people and meet them where they're at. So instead of giving a pitch about why they should use our enterprise solution because it has so many great features, we start the conversation off with questions about how they use GitHub in their personal life, what exactly is the open source project that they’re working on, and if it’s code that they’re going to use at work. The reason being is that I want to get an understanding of where they’re at before I give my elevator pitch. However, every prospect’s style is different. Sometimes, people will just be like, ‘Nope, just tell me what GitHub does.’ If that happens, I start at a really high level.”

“As you all are practicing your pitch, just know that it’s okay to fail often. Honestly, that’s what it’s all about. When I first started in sales, I was like, ‘Oh, I have to say my pitch in this exact manner. I’m young, so I need prospects to see me as a mature sales rep who has been doing this for years.’  But eventually, one of my first managers sat me down and gave me some of the best advice I’ve ever gotten: ‘Imagine you’re talking with one of your best friends over wine. That’s how your pitch should be -- conversational.’ So just relax. It's not a high-pressure situation. Everyone's human at the end of the day.”

Key Takeaways: Tailor your pitch to the prospect’s specific situation, get an understanding of where your prospects are currently at, and talk to your prospects like you’re talking to one of your best friends over wine or coffee.

5. How do you handle objections?

“Back in the day, I cared a little bit less about being perfect. Try to think about taking calls that way. So imagine somebody answers your call and says, ‘Oh gosh, I just stepped into a meeting or I'm in the middle of a meeting right now and I can't talk.’ Normally, people would be like, ‘Oh my gosh, I'm so sorry.’ But what I would say is, ‘Oh, that's so strange. You picked up your phone during a meeting.’ Then I would let that sit for a few seconds.

Eventually, they’d be like, 'Uh, okay. I have a couple of minutes.’ Other times, my prospects would hang up right away, so I’d call them right back and say, ‘Oh gosh, we must’ve gotten disconnected. I’m not sure what happened.’ And they’d say, ‘Yeah, okay, go for it.’ Obviously, when you do this, don’t be rude. But it’s okay to play around with prospects a little bit. It’s okay to think logically about some of the things that prospects say to you, especially the stuff that stands out.”

Key Takeaway: It’s okay to call your prospects out for giving you an illogical objection.

6. How do you manage being a woman/person of color in sales?

“Most sales teams have lots and lots of white guys, but the good thing about sales is that there's a scoreboard. For me, I wanted to prove my worth through my actions. If I'm not at the top of that scoreboard, maybe I don't deserve the respect that I think I do. So I hunkered down and just thought, ‘Where do I need to get to?’ I once worked at a company where there was a pushup contest on the sales floor. And while they were doing that, I was the one on the phone closing deals. I was like, ‘I’ll let you do your pushups because I'm still looking at the scoreboard, where I want to be at the top and stay at the top.’ For me, I was very focused on proving my worth through my numbers so people would take me seriously.”

“In regards to micro-aggressions, they suck. But that doesn’t mean you should interrupt back. Because that won’t make it better. Let them finish. But make sure to speak up after. Don’t just let it pass. The only caveat here, though, is that you need to know which battles are worth fighting for.

When I first got into tech sales, I wanted my colleagues to feel convinced that I could do this. But did I feel that every day? Did I feel that every minute? Definitely not. There are moments that feel so strange. Even in my role today, I second guess myself like, ‘Oh, am I really here? Is this really my job? How did I get here?’ Just know that it's okay to doubt yourself sometimes, but make sure to take a step back, look at what you’ve already done in life, and, most importantly, believe in yourself.”

Key Takeaways: Prove your worth through numbers by working hard and hitting quota, speak up about micro-aggressions before they pass, and trust it’s okay to doubt yourself. You've got this.

7. How can you leverage Flockjay to make a move up in your career?

“Flockjay has more clout than you think. I've talked to a lot of different industry leaders who definitely know who Flockjay is. One of our newest members on the Sales Development team at GitHub actually came from Flockjay. And they’re probably a month or two away from a promotion. So lean into the coursework and lean into what you're learning.

You might not have sales experience right now, but you’ve invested in a program like Flockjay, which is giving you that experience. So during your interviews, talk about some of the skills you’ve acquired. Talk about some of the tech tools you’ve mastered. Use these things to your advantage. You should also use Flockjay to prove that you’re dedicated because you’re actually doing something to get into tech sales.”

Key Takeaway: A lot of leaders in tech sales have heard of Flockjay, so speak to the skills that you’ve acquired, the tools that you’ve mastered, and the level of commitment you’ve given during the program in your interviews.

Thanks again to Keshia for joining us to share her expertise, and to our Tech Fellows for submitting thoughtful questions and participating during the live conversation! We appreciate you.