Put Your Startup Through a Sales Bootcamp Part II

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

This is Part II. See Part I, days 1–5, here.

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!


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.


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?