Founding a Start Up: Mastering the art and science of sales

portrait of Chris Grouchy
Chris Grouchy is a 2016 Fellow Alumni & Co-Founder of Convictional, 2.2M seed round enterprise B2C YC graduate company. He talks to Scott about how a twice-rejection from Mckinsey sparked his founding journey. Mastering sales as a rep at Shopify Plus and an internship at Cisco unblocked the conventional possibilities that were traditionally encouraged in the world of commerce and business grads. From crafting the perfect cold email to land a job, building networks, and coaching other Y Combinator founders on the art and science of sales, Chris gives us an insight into the success and learnings of his journey so far.

Three tips for drafting a fool-proof cold-email 

Scott: You worked in sales at Shopify before starting your own venture. What advice do you have for salespeople and just people in general on how to write a really effective and really compelling, cold email?

  1. Depending on your situation and the type of person you are reaching out to, there are certain key points and components that come with cold-emailing dep. The way in which you choose to communicate and structure your cold emails isn’t solely identified for salespeople, but anyone that is trying to build a relationship with someone online.
  2. There are things that you can do to increase the likelihood of getting a response, like deliverability. This is not about the subject line or call to action, but more about the email getting delivered to the right address and person. By verifying people’s email addresses, there’s a high likelihood of your email being in the right recipient inbox. The second piece around deliverability is around rate limiting. You should only one email per minute to avoid triggering spam filters.
  3. Lastly is optimizing your subject line. The preferred option is making your subject line short and sweet and making it personalized but being simple at the same time. For example, going on someone’s LinkedIn page and finding something interesting, and using that in your subject line, can lead to a 90% open rate. Make sure to humanize your emails, especially when adding a call to action. 

Three pieces of advice for building positive relationships with Gatekeepers:

Scott: Do you have any learning experiences of developing positive relationships with gatekeepers EAS, within organizations and how that’s helped you in different points of your career? 

  1. Something very tactical that Chris experienced, and works tremendously well in building trust with gatekeepers is where possible, moving the relationship to a text. Although emails are a great way to communicate with someone, we have to understand that everybody’s inbox is cluttered. So texting can still be an effective form of getting in touch with someone who’s really busy, but the job to be done here is building trust with someone who’s gaining access to the person.
  2. Without respectfully crossing boundaries, moving the relationship to text breaks down the professional barrier. There’s a high chance of getting a response via text since people are always on the phone. So when you have the chance, move your relationships to texts to build the relationship faster, and get a response quicker.
  3. It’s great to move to text relationships because those who create a social relationship end up performing better for their clients.

Three lessons from beginning your career in sales: 

Scott: How did people react when you said you wanted to pursue a career in sales, to what extent do you think that there is a stigma that exists against people pursuing business careers as a career?

  1. Chris’s rejection from McKinsey made him really grateful because it opened other opportunities for him to explore sales. It took him away from experiencing and staying stuck in the world of management and consulting. It was clear that there were many more opportunities in the world of business that could be pursued. However, those were the only options showcased and monopolized at campus recruiting, and as a result, created this sort of culture around.
  2. Don’t fall into the following what others are going to do after university. Take the time to choose and explore the world of management and consulting. Chris mentions how he faced pressure based on the limited options and opportunities, as well as looking over to see what everyone else was doing. The best thing to do is reflect and work around your strength-based skills, for Chris, it was connecting with people and coaching them.
  3. Lastly, Chris suggests throwing yourself into the field that you’re trying to get into. Chris realized with sales, it wasn’t all about convincing people to buy, rather it was about understanding their ideas, educating people on strategies, and creating economic upside. You dedicate yourself to understanding the art and science of mastering these skills and learning through the experience.