The Early-Stage Sales Rep: Surprising Traits for Success
Early-stage sales is a highly intellectual and cross-functional role that requires softer, more multifaceted traits outside of being competitive, hardworking and thick-skinned. Successful sales hires are also genuine and creative listeners with passions outside of work.
Despite being well into an enduring renaissance of entrepreneurism, starting a company still has a fresh and alluring connotation. Building a company beckons idealized and romantic images of opening an office, designing a logo, onboarding eager employees, and putting the final touches on a nearly perfect product or service.
Yet as you and other startup founders know, scaling a business is gritty and often unglamorous. More than any other function — marketing, product, HR, or finance — a startup needs two vital, basic organs: engineering and sales. Engineering creates the product while sales acquires customers. Without a product, a startup is just an idea; without customers, it’s just a product.
After engineering builds a product, you’ll often lead go-to-market strategy until you budget for a dedicated sales team. In order to hire successful sales reps who bolster your brand and bottom line, however, you need to appreciate the significance and complexity of early-stage sales.
Early-Stage Sales Hires
A lot of literature lists the traits that make an effective sales rep: competitive, hard-working, and thick-skinned. Many of these theories, however, are based on outdated notions of sales teams as aggressive armies knocking down the walls of Fortune 500 companies. Contemporary startup sales, on the other hand, is highly intellectual and cross-functional. Sales hires at early-stage companies aren’t simply selling. They are building business while loosely serving as marketing and product management; they fill the top of the funnel and raise brand awareness, while relaying firsthand UX feedback from customers to engineers, for instance.
Given the many hats that an early-stage sales team wears, its profile is nuanced and multifaceted, stemming from an array of backgrounds. While prior sales performance and the aforementioned traditional qualities — competitive, hard-working, and thick-skinned — still underlie successful contemporary sales reps, other more out-of-the-box, softer, and somewhat paradoxical traits are equally important to mix into a sales team:
I have always used my hands frequently and spoken in an excitable tone. Early in my sales career, a manager advised me to stop doing both. While this feedback was well-intentioned and complemented by very helpful constructive criticism, it ultimately backfired; as soon as I controlled my mannerisms and voice tone in my sales process, I lost my authenticity. While more professional, my presentation style was muted and dull. I connected less with clients, closed fewer deals, and learned that you need to be yourself in sales and hire similarly genuine sales reps. As buyers and senior executives are inundated with vendor meetings, pitches, and follow-up collateral, they’ll remember the unique and sincere salesperson over her more robotic counterpart.
Takeaway: Celebrate rather than shun authentic and differentiating quirks in your companies sales team.
The first startup company I worked for hired me despite the fact that I had no sales experience. They took a risk on me largely because I had played varsity soccer in college. As they had predicted, my athletic background instilled a strong work ethic within me. Yet I soon noticed that my complementary prior experience acting in theater and performing improv helped me succeed at sales equally if not more; in addition to equipping me to think on my feet while selling to clients, it enabled me to adapt my sales process to pricing changes as we iterated our go-to-market strategy and to develop new approaches to increasing revenue streams. While regimentation can significantly benefit a salesperson at an established company, creativity will better behoove an early-stage rep.
Takeaway: Seek early-stage sales reps with creative backgrounds and interests in addition to athletic profiles.
Some companies herald the disgruntled salesperson hunched at her desk past working hours because she’s behind quota; yet overwork and consistent underperformance are often a vicious cycle. One of the most successful sales reps at my former startup ran a coffee shop in Brooklyn while another taught boxing classes in between taking his kids to basketball practice. Salespeople who lead well-balanced, passionate, diverse lives bring efficiency to their sales process, positive energy to their clients, and fresh perspectives to their customer acquisition strategies.
Having outside interests also means that a salesperson is curious and will seek to really understand a client’s business model and needs. A curious salesperson is also more likely to contribute cross-functionally to company growth through product or marketing initiatives on the side of their more pointed revenue mandates.
Takeaway: Encourage your early-stage sales reps to instill work-life balance and pursue outside passions.
When most people think of sales, they picture a gregarious rep enthusiastically pitching. Yet so much of selling is sitting back and doing the opposite: listening. It’s equally important for a salesperson to have listening ability as it is presenting prowess. Actively listening enables reps to strategically consult with a customer or prospect, truly understand their pain points and effectively foster the most mutual value.
Similarly, salespeople are often deemed talented truth evaders, able to skirt around accurate answers through deflection or sheer bravado. Yet a rep’s ability to admit ignorance is key to long term success. A simple “I’ll need to confirm with my engineers” or “let me circle back with my broader company team” goes a long way with client inquiries; it legitimizes every answer a rep previously provided to a question and builds trust with buyers.
The most quota-crushing rep at my last company was an especially calm, emotionally intelligent listener. To paint a better picture, she was a yoga practitioner and animal rescue volunteer outside of work, an atypical sales profile. Yet this rep was so adept at knowing when a prospect could be pushed to close versus when that prospect earnestly needed more time to gather budget. If she tabled conversations with such prospects, she would keep them warm through avant-garde thought leadership and marketing before quickly closing deals when timing aligned.
Takeaway: When interviewing early-stage sales reps, ask them to follow-up with you in a specific manner (i.e. to send an article or text instead of email) and see if they act accordingly to test their listening skills.
An effective salesperson can make or break an early-stage startup’s success. As such, founders must prioritize hiring and nurturing representatives who can tackle this challenging, intellectual and cross-functional role with sincerity and creativity complemented by an ability to listen to clients and leave work on time.
What are the characteristics that you’ve found to make successful early-stage sales hires? Any surprising traits or personalities? Share them in the comments below or tweet them at Underscore VC:The best early-stage sales hires are... Click To Tweet