Put Your Startup Through a Sales Bootcamp

How I put myself through 2 weeks of rigor to get the sales machine set up, and how you can, too.

As a start-up founder, it’s easy to get caught in the “if-only” trap.

“If only… I was in an accelerator. Then I would have access to the expertise I need to set up the right sales funnel.”

“If only…I had some funding so that I could hire a sales person. Then we’d sign so many clients.”

Inevitably, there comes a point when you realize that “if only” is holding you back and there’s only one way forward- figure it out yourself.

That’s where I found myself with my startup, Welnys. We have a launched software product and some paying customers, which means now we’re focused on growing our customer base and revenue. But, I faced two problems. One, I don’t identify as a “sales person” and felt held back by my lack of expertise. And two, as a solo founder, I wear most of the hats, which meant that focusing on sales often took a back seat to defining our next feature set, project managing the tech team, working on my pitch deck, meeting with investors, answering emails… you name it.

But after hearing “we need to see more traction” from one too many investors, it was time to stop playing the “if only” game and start playing the “let’s do this” game. I came to two realizations. First, I while I knew that sales was my priority (as Daymond John says “sales cure all”), I recognized that I wasn’t treating it that way based on how I spent my time. Secondly, there’s no reason why I can’t access experts on my own and train myself to set up my sales machine. So, I decided to put myself through a two week sales bootcamp. I would design a curriculum, line up experts, clear my schedule and commit to this process the same way that I would commit if I was attending a bootcamp run by someone else. This is how I did it, and how you can, too.

Day 1, Monday: Set up the experts

I went through my Linkedin to see who I knew that I could bring in for expert help. I located about six people this way, but none of them replied to my Linkedin message. I also posted a request for experts in a few business groups I am in. I was more successful here, I got four replies and two meetings (with Molly, a digital marketing expert, and Adrian, a sales process expert). Finally, I went through my own contacts and realized I know some sales people and even content marketers. I contacted four people this way and two more agreed to meet (Tom, in enterprise sales and Ujjaini, in advertising). In total, I reached out to 14 people and got four meetings.

I also bought a few books to use as reference:

Day 2, Tuesday: Finalize pricing model, market positioning and GTM

To get set up for the next steps, I knew that it would be important to finalize my market positioning and go-to-market plan so that I had a solid north star to follow when making decisions about which sales channels and messaging to use. This became incredibly useful as a reference point on some of the other days, so don’t skip this step. I used Obviously Awesome: a product positioning exercise, which was a helpful framework.

I also completed my pricing strategy, which I had been fine-tuning with the goal of having clear unit economics with margins of 60%. Once this was done, I was able to complete the Are You Ready to Scale worksheet, which I obtained from Donna Levin, the former co-founder of Care.com and MIT entrepreneur in residence.

Day 3, Wednesday: Sales Tools

This day was spent getting my tools in place. I put together a list of tools like CRMs, email automation, SEO optimization, analytics and more. I was grateful to find a series of posts from Zapier on best CRMs which I found trustworthy and helped to cull the available options. I also leveraged this presentation on Growth Hacking which lists many tools. My research is available in this google doc, feel free to use it.

I knew that picking a CRM with email tools was the most critical step for me right now, and I was worried about losing a bunch of time to researching each tool in depth as I am wont to do, so I decided to just pick one because I can always change later, and my goal right now is to just get things up and running. So I went with Zoho because two other entrepreneurs recommended it to me. Sometimes, you just gotta keep things moving!

Day 4, Thursday: Create sales materials, presos, scripts and process

Today I brought in Adrian Miller who is a sales consultant and trainer. Adrian suggested that I should outline my sales process — she calls this a “situation analysis.” As soon as she said this I realized that I didn’t really have a process. I do something different every time I pitch a customer, where I should be using a standard operating procedure (template email, what happens in the first meeting, how do I follow up from the first meeting and with what materials? What happens in the second meeting? How do I follow up from that meeting? and so on….) She also recommended that I engage a sales coach to help me navigate specific situations as they come up (overcoming objections, for example).

I also met with Tom Cheriyan who is in enterprise sales. Tom helped me to realize that my sales materials need to revolve around value. Many customers we are pitching have the budget- so their question is more “is this of value to us?” He suggested I add an impact slide to my sales presentation “X issue costs companies $X” to drive the question of value home. Much like Adrian, he also gave me advice about how to fine tune my sales process- like always setting an agenda to define the topics of the meeting, what to do on the first meeting (ask and listen), second meeting (demo) and third meeting (sell).

Resource: The Greatest Sales Deck I’ve Ever Seen

Day 5, Friday: Digital Advertising

Today I brought in a few of my experts to discuss digital advertising. An acquaintance of mine, Ujjaini, who was formerly in advertising and is now a human-centric designer, urged me to start with research. I need to know more about my customer. Who are they? Where do they hang out after work? What do they do on the weekend? What do they read? Successful ads are hyper-focused, and that can only be done with an understanding of my buyer. She recommended that I use this research to create an opportunity statement: “A (blank) needs (blank) because (blank).” I could then use this opportunity statement to craft a few ads to A/B test. She also pointed out that I need to define the goal of the ad, which could be different based on the customer I am targeting. Is the goal to convert on the page or to capture a lead?

Next I met with Freddy from Novofex. Much like Ujjaini, Freddy felt that there was pre-work that needed to be accomplished before I could start advertising. He recommended I spend some time to update my website to tell customers WHY they should use us instead of just WHAT we do. He also recommended generating 6 pieces of content that would live on 6 different landing pages on my website that we would then drive ads to and capture leads.

Freddy recommended that I plan out my digital sales funnel. Where will customers interact with me? In what order will they interact with me (ad -> landing page -> content -> website -> pre-demo -> demo -> meeting)? What do they want to know each step along the way? Where and how will I capture leads and how do I engage them once I do? Once this homework is done, only then can we begin to test some ads.

Finally, I brought in Molly who is the digital and content marketing manager of Synap. Molly was surprised I wasn’t including Google ads as part of of my strategy. She explained that even though LinkedIn is where my customers are, it’s not where they are researching software- that’s Google. Like Freddy and Ujjaini, Molly felt that content was the right place to start. She encouraged me to set up a blog on my website where I could start establishing domain expertise.

Additional resources:

By the end of this week I had created an artifact, a deck that outlined:

  • Our unique features
  • How those features translate into value for the customer
  • Who my best target customers are, why they love us, how we reach them and who the decision maker is
  • Pricing model
  • Digital marketing process
  • Sales process
  • Sales channels
  • Customer personas

This was week 1 of my bootcamp. Read part II, days 6–10, here.