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

Week 2

Day 6, Monday: Content Marketing

I’ve noticed one refrain from everyone I’ve talked to: “I would start with content.” I’ve been told this by sales people, digital marketers and growth hackers. So, I was especially interested to dive in today.

First, I set up the tools- I decided I am going to Medium’s custom domain functionality and integrate it on to my website (an example of how this looks here). I was worried about SEO being an issue, but this post on how to manage SEO and Analytics on Medium put my mind at ease. I set up an IFTTT to autopost any Medium articles I write to LinkedIn and Facebook.

Next, I created a list of 31 story ideas/headlines, once again drawing largely from my Day 2 exercise around what our target customers care about. I’ll write 5 of them now to serve as content to power my digital marketing campaign, and the other 26 I will plan to publish once per week. This is a half-year worth of content. I created simple table listing article headline, submit date, publication date, original publication location and secondary publication location (for repurposing) and finally associated keywords.

Next it was time to think about partnerships. I could partner with bloggers and thought leaders to allow them a platform to post on, or vice-versa. This will help drive traffic to my site and help with domain authority for SEO. For now, I simply made a note in my editorial calendar to explore this after we have some live content. When it is time to tackle this, the first place I will start is with Welnys’ existing provider network. We already work with 500 wellness providers who will want to contribute.

Another component of our content strategy might one day be a newsletter. We already have a pretty robust mailing list, but I feel that focusing my energy on a newsletter will be easier once we have regular blog content that we can cross-post. For now, I’ll add a newsletter sign up to my website, and I’ll add a note in my editorial calendar to start a newsletter in a few months.

Additional resources:

Day 7, Tuesday: Create DRIP Campaign and source emails

I spoke with one of my advisors about this project and he gave me a piece of advice- don’t start my digital marketing until I do my email campaign.

“Why?” I asked, “because it’s cheaper?”

“No,” he replied, “because it will tell you if your messaging, target market and landing page are right. You need to know that you have those things right before you start scaling with advertising. Email lets you A/B test before you start spending.” He also recommended that I set goals: x% open rate y% click rate and z% conversion rate so that I have something to optimize toward.

I started this process off wrong. I began writing subject lines and crafting emails, and then I realized- there wasn’t any PLAN to what I am doing. So I took a step back and began by outlining the process.

  • What is my goal?

  • Who is my target audience? (I had already determined this on day 2)

  • How many emails will I send and what is goal, trigger and timeline for each?

  • What happens if they open? If they don’t?

  • How will I measure results?

From there it was much easier to come up with campaign ideas, subject lines and email content.

Additional resources:

Day 8, Wednesday: SEO

Today I met with Eben, an SEO expert. I was worried that SEO was going to be a huge and daunting project, so I relieved that he was able to outline a simple plan to get me 80% of the way to successful SEO.

  1. Add title tags to every page on my website

  2. Identify relevant keywords and target those keywords with dedicated pages with lots of high quality, relevant, useful text content

  3. Use content marketing to build backlinks

That’s it!

Resources:

Day 9, Thursday: Channel Partnerships

I was really hoping to speak to an expert today about channel partnerships, but I could not find one. This is a strategy that I will have to continue to work on to learn about best practices and how to structure a partnership. For now, I simply worked on my pricing models to make sure that I could absorb a channel partnership pay-out and at what percent. I also took steps to identify a number of potential partners and think through what a proposal might look like. I considered:

  • Value to the partner? To Welnys? To the end-user?

  • Risks and how to mitigate them

  • Technical dependencies and requirements

  • How to track metrics and sales

  • Channel partner payouts and resulting margin to Welnys

  • What the partnership looks like (what are we selling and how)

Additional Resources:

Day 10, Friday: Social Networking and Press

Today I didn’t dive as deep because press and social are not key to our current goals. But, I wanted to note some tools and strategies which I will explore in more depth at a later date.

Getting press has always been a strong suite of mine- when I ran my first business, Fumee, a cigar bar, I was in Cigar Aficionado, Cigar Magazine, Cigar Snob, The Wall Street Journal and more. I did this mostly by just pitching stories. I was always surprised by how often it resulted in coverage. I plan to do the same this time around using tools like HARO (Help A Reporter Out), Hey Press, PR Press Hour and Just Reach Out, as well as cultivating our own internal list of press and publications.

For social, we looked at each channel and thought about where our target audience lives. They do NOT live on Snapchat or Twitter. They DO live on Facebook and LinkedIn. They MIGHT live on Instagram.

Since we have limited resources we also want to pick a channel that will be easy to create content for. While we do have a visual business, taking and editing interesting pictures for Instagram is a time suck. Most of our target audience (HR and office managers) are heavy LinkedIn users, so we will start there. Our simple strategy for now will be to join relevant interest groups and repost content that we’re already creating for the blog. This is the minimum viable effort for now.

Conclusion

I’ve learned a lot through this process, and it’s a good start, but now each item needs to be executed on. The next step is to create a timeline and roadmap of all the associated tasks and get to it!

I’d love to hear from you. What did I miss? What other books or resources do you recommend?

Originally posted on Medium Part I and Part II

musingsHeather Waibelsales