Office Hours: I was the former VP of Global Sales at Eventbrite and am now Chief Commercial Officer at Brandcast. I'm Chloe Stewart.Featured

Hi everyone! I’m Chloe Stewart, Chief Commercial Officer at Brandcast, a software as a service based content management system. Prior to Brandcast, I was Vice President of Global Sales at Eventbrite and worked in sales leadership roles at GoGrid Cloud Computing and Learn iT!I have a degree in English and Women’s Studies from the University of Wisconsin Milwaukee and have a Master’s Degree in Gender Studies from San Francisco State University.Ask me anything about sales, go to market, leadership, and more!
Thanks so much for joining us @chloestewart!Elphas – please ask @chloestewart your questions before Friday, February 12th. @chloestewart may not have time to answer every questions, so emoji upvote your favorites πŸ”₯πŸ‘πŸΎβž•
Hi Chloe! Great to meet you! I recently pivoted my career into Sales after 15 years across a variety of roles in Human Resources, Product Marketing, & Corporate Venture Capital. What advice would you have for someone entering Sales mid-way in her career? Also, what is something that you know now, that you wished you learned earlier in your career? Thanks!
Wow, I'm so impressed by your background -- you must be an amazing resource to your friends and colleagues!The best salespeople I know embody a handful of key traits: high EQs; masterful storytelling and problem solving skills; impeccable active listening skills; fantastic communication; project management/organizational savviness; self-disciplined and motivated. Sales is not a career path for those of us who want to slide by and input absolutely informs output. A healthy dose of fearlessness also sets the best sellers apart from the rest and I'm happy to share more about what that looks like in practice.When I started in sales, I wish that (soooo many things, but I'll stick to three):1) I would've spend more effort planning my time so I could maximize outcome-driving activities.2) If I was going to lose a deal, lose it early3) No one else owns my success but myself. I'm my best and, sometimes, only advocate. This also goes for my customers: it's my job to be their advocate and to prioritize their success.
Thank you @chloestewart!!!!
Love that your degrees are in liberal arts. Do you have any commentary on that vs. MBA, etc.?
Honestly, I wish I had both and often think about going to business school. That said, I owe so much to my education (and, ultimately, my privilege for providing my education in the first place) and to the liberal arts. Skills such as critical thinking, self-expression, problem-solving, etc. coupled with developing empathy, curiosity and connectivity have inherently informed my professional career.
Hi Chloe! Thanks so much for doing this! What advice would you give to the first Sales hire at a Growth-stage startup? And, what are some pitfalls to look out for?
How exciting! You have an opportunity to make a massive impact and that can be both exhilarating and slightly terrifying (spoiler alert, I love this sort of stuff). Prioritization is CRUCIAL, which is easier said than done sometimes.1. There will be A TON OF STUFF TO DO and sometimes it will be hard to easily identify what you should focus on. -What is your primary goal and what are the leading indicators to help you track attainment of that goal-Getting super crisp on these metrics and aligning on them with your leader(s) should happen right away. Center your (consistently scheduled) 1:1s with your manager around these metrics.-All of the work that you do and all of the tradeoffs you make will be in service of prioritizing the attainment of these metrics.2. Learn your product/service asap. -Presumably, your founders or CEO have done most of the selling at this point and have established a level of product market fit. -Be selfish and make sure you receive all of the training that you need to confidently represent the company as a product expert. -You also need to nail the competitive landscape. Specialization is so important when startups are still establishing brand identity and awareness in the market and the first sales hire is implicitly one of the business' key brand ambassadors. Prove that you know what you're talking about.3. Prospecting is a lifestyle. -What's your ideal customer profile (ICP)? Who are your target accounts? Who are your buyers within those accounts? What do they care about and why should they care about you?-In order to drive results, you have to focus on the right segments, companies and buyer personas and then spend the time/effort targeting them via different channels (email, social, video, CALLS -- yes, calling is still the most effective engagement tool --, etc.) -Another piece of advice is to leverage referrals and warm intros as much as possible: get intros to your investor's portfolio companies, comb your colleagues' LinkedIn connections and ask for intros, comb your own connections and ask for intros, etc. -We also know that our buyers are inundated with information on the daily and salespeople are still learning how to adapt to a remote selling. Every touch point matters and you (potentially) have the added complexity of still establishing your company's brand. You got this, I'm rooting for you!
Thank you so much Chloe!
With your (rare?) expertise in both Gender Studies AND marketing, I would love to hear your thoughts on how we can sell American women on using their dollars as an instrument of activism--by spending on Gender Fair companies, or the top 10% of public companies with okay gender metrics.. Every day, women spend millions of dollars on misogynist companies--perpetuating systems that we fight against. The human Rights Campaign changed the workplace for LGBTQ people with a similar index--how might we embed the same idea?
Hi @amycross, thank you for raising this question, it's so important. Here are just a few thoughts:-More diversity in leadership positions (gender diversity, BIPOC, LGBTQ) enables the prioritization of messages like this one and creates messenger credibility. If I'm encouraged to support Gender Fair companies by a business with a sea of white, cis-male faces on their About Us page, I'll have lots of questions. Representation matters. -Partnerships can be incredibly effective here. Creating alliances to co-market messages like this one helps spread the word faster to a larger audience. More impact.-We have to avoid 'splaining and create real value for our audience. Who are we specifically asking to support these companies? Why? How are we ensuring the message hits the mark? There are Gender Fair companies on this list that lack great track records when it comes to LGBTQ and BIPOC representation. Intersectionality is crucial.
I'd love to, if you don't mind, hear your story about your journey, from after you graduated in your studies in English & Women's Studies to your first role in sales. When did you know you wanted to pursue a career in sales?
Hi @WenlinT, thanks for asking about this. Had you asked me while I was in college and grad school if I imagined myself with a sales career, I'd have looked at you like you were from a different planet. I fully expected to teach Gender Studies or something within that realm at the university level and really just stumbled into sales. When I finished graduate school, I was broke as a joke and took the first job I was offered ... which happened to be in sales. My plan was to save some money while researching/applying to doctoral programs. However, this was right before the 2008 financial crisis and we saw the early impact on academia, namely the defunding of more marginalized fields, like Women's Studies, Cultural Studies, etc. I had a bit of a mid-twenties existential crisis and decided the risk of going back to school for another ~6 years without any real job security (tenure) was too high. I was still working at my sales job and, with the decision to pause the pursuit of doctoral programs, I focused on paying off some debt and, in so doing, really learned my trade. Fifteen years later, I'm still in sales!Sales interests me for all the reasons you often hear: problem solving, relationship building, advocacy, cross-functional collaboration, insight into different businesses/industries, etc. What I also appreciated and continue to appreciate about sales is that -- and this is a massive generalization, so forgive me -- there can be less of a barrier to entry than, say, starting a career in Product or Engineering. I know many salespeople without college degrees or with Liberal Arts degrees. I know salespeople who spent years in the service industry or teaching high school or working for nonprofits. Finally, have a graduate degree in Women's Studies absolutely helped me as a professional, as a salesperson and, ultimately, enabled me to advance my career. Grad school gave me discipline, rigor and communication skills. Women's Studies educated me on power dynamics, intersectional and transnational feminism, global economics, etc. My education shaped my ethics, values and politics and I don't leave these out of my workplace.
@chloestewart I'd love the opportunity to chat with you more about Eventbrite, sales, and go to market strategies. I will connect with you on LinkedIn now.
Sounds good, Nicole!