Cold Outreach Methodology

Danny Leonard
Bootstrapping Sales
6 min readMay 4, 2017

In this installment of Bootstrapping Sales, we’ll share techniques and specific frameworks for you to act on your Research and Lead Generation efforts and test out your customer profile hypothesis.

Value Proposition Targeting

Your research should have yielded one or more profiles as potential leads for you. Now you’ll want to figure out where they live and if they find value in your offering.

No, you don’t need their home address, and you certainly don’t want to stalk them or their families, but you will need to pay attention to where they are each day.

Ask yourself the following questions to better understand the correct direction for your outreach:

  1. Where does my prospect spend most of their day? (a desk in front of a computer? on the phone? in surgery? behind a movie camera? at a retail shop? etc.)
  2. What modes of communication does my prospect prefer (email? LinkedIn? Facebook? snail mail? Snapchat?)
  3. Are there any available public examples of reaching out to my prospect where they get responses? (responses on Quora? public email replies? retweets?)

Let’s crystalize this with an example. Say your product is a SaaS dashboard that helps celebrities attract more sponsors, using the three questions above you would answer:

  1. Running errands, getting coffee, having lunch, etc.
  2. Twitter, Snapchat, Instagram, their managers
  3. Yes! TWTR & Instagram

Putting it all together, your outreach hypothesis would read something like this:

Since my targets are celebrities, I need value propositions that can be communicated to my prospects through Instagram, Twitter, Snapchat, and through their managers.

So What Do You Actually Say?

Your value propositions are dictated by your Research and Lead Generation. Craft each value prop succinctly and cater them directly for the ‘who’ you’ve already uncovered. Again, using celebrities as an example here, a potential value prop could be “we’ll guarantee new sponsors within 30 days.” What an incredible product for celebs (I know, right?!).

Next, list out all the potential value props that could attract celebrities to your business. Follow the process below by using our handy Value Proposition Framework:

  1. List out all of your value props
  2. To the best of your ability, determine all potential prospect objections/concerns. This list will become more robust as you engage prospects and collect data points
  3. List questions that would lead your prospect into talking about your value prop in a positive light
  4. List reasons why your value prop would help their business
  5. List reasons why your value prop doesn’t actually matter to them
  6. Repeat 1–5 for all value props
  7. Start your outreach with the strongest value prop over a cadence specific to your audience

Use these value statements in your outreach and track your success. Since it can take 7+ touch points to generate a sales qualified lead, stick with your value prop tests through the “No’s” and no responses.

Remember that you develop your outreach plan based on a hypothesis, so it’s critical to track the plan through at least one cycle (e.g. 10 touch points in 8 weeks) so that you learn what you need to tweak to make the next iteration of your outreach plan more targeted.

And How Do You Say It?

The purpose of a cold outreach campaign is to close deals, eventually. In today’s sales world where buyers have information overload, you can’t go straight for the jugular. Starting a value filled dialogue is the way to go, 99.995% of the time.

To create that dialog, keep these six best tips in mind when writing your scripts:

1/ State your reason for the outreach up front. As in, after you say “hi,” spell out something that says “the reason I’m reaching out is…”

2/ Your time vs. their time

  • qualify for time to establish mutual ground. Literally script out: “Is this a good/bad time to chat?”

3/ Name calling ;)

  • Mention your prospect by name. It’s polite.
  • Mention their name, at least once per message. And it doesn’t always have to be at the beginning.

4/ Don’t sell, help. Seriously.

  • Look at the LinkedIn profile of the person you’re approaching and think about what they would like to hear. Try to learn something about them to make a personal connection. You don’t like to be sold to; no one does. So ask yourself, “would I open, read and respond to my own email or cold call?” If the answer is no, you need to go back to the lab and rewrite.

5/ Be bold. Be human.

  • I mean, we shouldn’t really be talking about this but here we are. If your script sounds robot-like or is filled with buzzwords, it’s probably because it is. If it sounds too formal…you catch my drift. You should make massive statements of value (e.g. we’re changing the way the world thinks about ___), but never forget that you’re reaching out to another person. Be kind, be humble and above all, be bold and be human.

6/ CTA

  • Every touch point you have with a prospect must have a call to action (CTA). If your outreach doesn’t have one clear CTA, well, now you know why your prospect hasn’t responded to you yet.

Outreach Calendar

This is where you put it all together. Physically write out the schedule of when, where and with what you’ll approach your prospects and set up your tracking.

This will help space out your cadence and enable you to tactically parse up your results. Ensure whichever method of outreach you choose for your targets, you have a proper metric that’s achievable to go along with it.

Closing a prospect on your first touch point is rare, therefore “Closed Deal” is not a proper metric. Set an achievable and measurable hurdle to start — “Replies” is a great metric for messaging mediums (email, twitter, LinkedIn, etc).

Track each of your metrics on a daily basis on your calendar. Your outreach calendar needs to be long enough to build a statistical significance of evidence to prove or disprove your hypothesis.

For emails, statistics show an email outreach campaign should be more than six stages as >30% of replies come stage seven and beyond.

For calls, we use >200 calls/week over six weeks.

For newer sales mediums, like LinkedIn or Facebook message, due to their personal nature and limitations on services (InMails/month for LinkedIn) you’ll need to tweak appropriately.

Lastly, if you’re approaching enterprise customers, your sales cycle may take many months or even years. Adjust your calendar accordingly.

The finished calendar should look like this framework — feel free to use and steal this template.

Tracking

If the minimum viable success is converting at 1.5% and if your goal with getting sales off the ground is to grow your company beyond a sole proprietorship, then you’ll want to set yourself up for a scalable sales process.

When we say scalable, we’re thinking of the next step in growing your business which often means hiring two or three sales reps, max. And as long as we’re on the topic of hiring, you can start hiring if and only if and when you’ve proven two things:

  1. There are enough leads now and a scalable way to generate leads for one rep for an entire year
  2. The converted leads produce, on average, deal sizes large enough to justify the additional headcount.

We’re not talking about setting up NASA level analytics, but you’ll want to track one metric above all else: your close ratio, aka “prospect worked to close” ratio.

If you want to get fancy, we recommend tracking “prospect worked to connected” and if applicable “connected to demo” ratios as well. We’ll layer on a few other metrics in a later article, but this will be enough to get you started.

Sales Tools

You can track your sales efforts with $0. Really, you can. It might take a bit more time on the admin side of the things but a mix of email, calendar reminders, a spreadsheet and perhaps a note taking app will do the trick.

Having said that, we highly recommend a CRM. If you can afford to spend $10–50/month, you’ll be able to automate much of the mundane tasks that come with tracking your sales. Plus you can have analytics at your fingertips with a press of a button (or three).

There are two key aspects to tracking your sales efforts: sales email automation and CRM/reporting. Below is a list of tools we’ve used and recommend depending on your preference and workflow.

1/ For sales email automation, consider:

2/ For CRM and reporting, consider:

What you’ve built thus far is a potted plant. Now it’s time for the proper amount of water and sunlight to see if your plant will grow.

We love hearing from you. Please continue sharing successes and war stories with us. Any and all feedback is most welcome.

Need help Bootstrapping Sales? Contact Danny for help bootstrapping or scaling sales and Nima if you’ve been bootstrapping so far and are now considering raising capital.

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Danny Leonard
Bootstrapping Sales

you're not gonna do big things, unless you do big things