The Top 3 Superpowers Startup Sales Reps Need to Have

My hometown of Toronto has been a great place for world-class startups to grow and flourish, and I’ve been fortunate to spend the majority of my career across four of the best ones. The journey of working with amazing entrepreneurs and building out sales teams has meant a great deal of hiring and put me in touch with all types of sales professionals.

I’ve often said that sales teams are like collections of superheroes, with each team member bringing their own unique set of superpowers. While characteristics like listening, genuine curiosity, drive, relationship-building, and business acumen are key ingredients for sales success, over time I’ve found that in order to be effective in the fast-growing, ever-changing, world of startup sales, reps need to bring three key characteristics to the table (I call them, the three Cs of startup sales).

1. Conviction

Inertia, the resistance of an object to any change in its state of motion, can be the death knell for a startup.  Inertia makes people or organizations tend to do exactly what they’ve always done in terms of investment, technology, or process. That’s why the most effective salespeople in these environments are the ones that are able to muster a high degree of conviction in their solution. To challenge, educate, enlighten, support, and lead their customers to a new experience.

While most people are generally risk-averse, the role of the startup organization is to help people understand the value of crossing a chasm and the responsibility for acting as an agent of change, usually falls to the sales team. For instance, they might challenge customers to move from an in-house technology model to the cloud. They might challenge job seekers to post their resumés online instead of mailing or faxing them to potential employers. Or, as in the case of social media, they might challenge people’s perception of the foundational behaviors they engage in online.

These type of reps typically operate with more passion and conviction than most and are well-equipped to field objections and concerns. If you want to be a successful startup sale rep, cultivating a high-conviction, challenger mindset will help you execute with massive credibility and drive success!

2. Coachability

Early on at my third startup, I connected with Mark Roberge, then the VP of Sales at Hubspot (and now the author of one of my top sales reads). Having a business consisting largely of super-smart MIT grads, Mark’s perspective on the scientific approach they used to determine which characteristics correlated most consistently with top sales performance was amazing. Number one on their list: coachability. To this day I’ve found the importance placed on this trait to be extremely well-founded.

Coachability speaks to the candidate’s ability to listen, and both understand and externalize knowledge quickly. After all, in the world of complex sales the last thing you want is a sales rep who executes the same play and talk track regardless of the information and queues they’re getting from the customer. This is especially important in a startup environment where the process and playbook are constantly being refined and reps may find that sales tactics that worked just a few months ago, no longer do.

Much like an athlete, this discipline also requires that the sales rep be open to coaching and continuous improvement. While you can assess a candidate’s coachability by asking them to provide historical examples of where they were required to learn and assimilate new knowledge quickly or instances where they incorporated feedback provided by their manager, I prefer to assess the candidate real-time in the interview itself. I’ve found my coaching test works great, but you can leverage any exercise that requires the candidate to incorporate real-time feedback.

3. Creativity

Hey, if selling things was easy we’d pay high school students minimum wage to do it instead of looking for experienced professionals who we incentivize with highly lucrative compensation plans! The fact is, selling things is hard and the path to success is rarely as clear as we hope. With most sales cycles fraught with unrelenting adversity, the ability to think creatively is paramount. Double this in a startup environment where you’re often writing that playbook as you’re executing it!

Creativity speaks to a candidate’s ability to adapt and explore solutions that move deals forward when faced with a challenge. Sales reps routinely field objections around things like cost, sources of urgency, and the need for lengthy free trials, but being able to comfortably handle a broad spectrum of challenges with less obvious resolutions is often a better indicator.

For example, suppose you’ve been selling to a customer who has confidently told you on many occasions that they have budget and decision-making authority to purchase your solution. However, as you get closer to the end of the sales cycle you realize they don’t have the power they claimed and to get the deal done you’ll need to engage with their executive team.

Unfortunately, if you call into the executive team directly, circumventing your contact, you risk seriously damaging the relationship with your champion and losing their support. Yet, if you don’t get above them, there’s no way you’ll win the business. What do you do?

The good news is that getting a sense for a candidate’s creativity is as easy as asking them to describe a time where they encountered a serious roadblock in a sales cycle and the creative approach they took to overcome it. When adversity strikes and the path is unclear, those with a mature sense of creative intelligence find a way to prevail!


While there are many qualities that successful sales reps possess, when it comes to startup organizations looking to introduce new products or services to the market, a keen focus on the three Cs of startups sales will put your organization on the right path to securing winning sales talent.

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