Category Archives: sales

Sales Meet Marketing

If you don't like what's being said, change the conversation.Up until Don Draper and Sterling Cooper started gracing our airwaves a lot of people did not understand the distinction between sales and marketing. Many still don’t. It is understandable as to outsiders they both have the same purpose: to get people to buy the product. Even in small companies where you might not have separate sales and marketing teams it can be confusing. As your company grows (or you find yourself working in one) you will find that the distinction exists and often for a good reason.

As an underdog entrepreneur it is important to make the distinction between sales and marketing early on so that when you do start hiring people for specific roles in those departments they are stepping into structure that already exists and build upon what has already been done instead of reinventing the wheel. So this is written with that in mind.

Sales -> Marketing

Sales gives marketing one crucial thing it does not have which is the customer’s voice. Sales talks to customers and potential customers all day every day. They hear what problems people face, what they are looking for in terms of solutions, and what it will take for them to pick your solution. In short, what sales can give marketing is information:

  • Any product questions
  • Most common objections
  • Current solutions/providers that customers use
  • Words, language, jargon that customers use

Additionally sales can, and might be already, monitoring their leads’ blogs, social media, and any news about them (you can use Google Alerts to do this for free). When they learn about problems that the leads face they relay those to marketing. If it is deemed that a decent number of customers would have those same problems then there might be a good opportunity for a piece of content.

Sales gives marketing one crucial thing it does not have which is the customer's voice.

Marketing -> Sales

The main thing that the marketing department can deliver to sales is content that helps them move prospects further down the funnel. This content can be product information pieces, materials that speak directly to customer objections, and industry/market data and projections. I think those last ones are particularly good for for what I call conversation pieces and can be turned into SlideShares that can be shared on LinkedIn and that sales can send to prospects that have fallen out of the funnel in order restart the conversation and bring them back in.

Here are some ideas for materials marketing can create:

  • Whitepapers
  • Ebooks
  • Slideshares
  • Infographics


It will take time but be sure to set up tracking so you know what each prospect has been sent and by who. This will help you cull the content that does not convert and double down on the content that does.


There will be some pieces that will be more effective if they can be customized with the prospect’s name and data. Content that has projections or comparisons to industry averages are examples of those. In those cases if possible give sales the content in a format that they can customize themselves.


The more data that is shared between sales and marketing the better each department will be at segmenting customers. That will allow more targeted communication and content which will result in more leads for marketing and more customers for sales.

Continuous Cross-Pollination

Without veering too far down the lane towards Office Space and TPS reports, it might be beneficial to have a set list of deliverables for sales to bring to marketing for a monthly meeting between the two departments. Those might include some of the things that we just discussed. Additionally once a quarter have marketing sit in on a sales meeting and vice versa. That sort of cross pollination can lead the kind of initiatives that deliver the big results you crave.

Sell more in January by asking your prospects about their annual goals

Time to set new year's resolutions for your business

Businesses often set annual goals or initiatives just like individuals set New Year’s resolutions to lose weight or read more books. A business is more likely to set goals to win more business, roll out new features or services, or improve a few key metrics. This is something that will be on the top of your prospective customers’ minds at the beginning of the year. This offers you an unique opportunity to try a different sales pitch.

When emailing prospects or making sales calls at the end of December or the beginning of January you can specifically ask them about their business goals for the year and if there is something you can do to help them achieve them:

Hey <prospect name>,

A new year is upon us and you may be setting goals to take your business to another level in 2017. If you have any initiatives for <the service or product you provide> I would love to explore helping you with them. We’ll help you achieve this goal early in the year which creates momentum for the rest of them!

I look forward to connecting with you soon.

<your name>

p.s. here is a <ebook, article, video, SlideShare, etc.> about <customer problem> that you might find useful.

Note that is email is not about you but all about your prospective customer. You are extending an offer of help and when you do get them on the phone do not launch immediately into your sales pitch. Continue exploring their business and their goals prior to offering your business as the solution. Listening to them will help you use the right language and frame your product/service as something built for their specific needs.

Like an individual who signs up for an annual gym membership but stops going in February, businesses also lose steam on their goals as more pressing matters come up throughout the year. With this in mind make sure you send the initial email in the first half of January and follow up at least twice before Valentine’s Day. Once March comes we’re already a sixth of the way through the year and we have many things vying to be our priority.

Like with anything email campaign test a couple different subjects and body content. This way when you repeat the campaign in twelve months you will get better results.

Good luck and happy New Year!

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Lost Deal Drip Email Campaigns

Sales is a challenge for many of us. It is the lifeblood of our business so we spend a lot time and resources on it. But the unfortunate reality is that most leads do not turn into customers. There are many reasons for this including they might be just window shopping and gathering information, they aren’t ready to buy, they use one of our competitors, or our product or service is not a good fit.

Behind all of those is a time component. Those all might be true right now but might not be true in the future after you have improved their product, your competitor has stumbled or not lived up to expectations, or they have moved forward in the buying process. A “no” now can turn into a “yes” later.

I saw this post from Jason Lemkin of SaaStr about drip marketing campaigns for lost deals and thought I would create a few email templates for you to use based on his suggestions.

10 months out (Renewal #1). If your competitor really screwed it up.

You’re hopefully rolling out new features or services at least every ten months and this email will bring attention to that. At the same time ten months is too soon to do another hard sell so this email just tries to sell the lead on a quick chat to catch up and find out how things are going.

{{ subscriber.first_name }},

I wanted to check in and see how things are going. We talked almost a year ago about <the problem> and you mentioned that you are using {{ subscriber.current_provider }}. How is that going?

We’ve rolled out some new features <or services> but are also continually looking to improve so learning a bit about what is working with {{ subscriber.current_provider }} and what, if any, difficulties you might be having would be very helpful for me.

Do you have five minutes later this week for a quick call?

Wed @ 9 am {{ subscriber.friendly_time_zone }}
Thur @ 2:30 pm {{ subscriber.friendly_time_zone }}
Fri @ 9:30 am {{ subscriber.friendly_time_zone }}


{{ from_name }}

20 months out (Renewal #2). If your competitor doesn’t remain competitive and deliver enough value.

At this point your business has hopefully matured and your product or service has improved significantly while at the same time your competitors might be big enough that they are not innovating at a quick pace or are slow to respond to customer concerns.

{{ subscriber.first_name }},

I hope you are having a great week.

You have been using {{ subscriber.current_provider }} for a while now and I wanted to check to make sure that is still going well for you. We have been aggressively adding new features <or services> that have been providing a lot of value to our customers and I think we’re very competitive with {{ subscriber.current_provider }}.

I would love to have a quick chat with you to see if we can deliver a higher value to you today than when we last talked and make <the problem> a thing of the past.

I hope business is going well and look forward with connecting with you soon.

Have a great day,

{{ from_name }}

30 months out (Renewal #3). If your competitor did an OK job but isn’t loved and you now are doing something much better (one thing) than them.

As a business grows its needs change and the reasons for picking a solution in the past might no longer be valid. While your competitor might have been a better solution three years ago you might better address the pain points the customer is having now.

{{ subscriber.first_name }},

I wanted to check in and see how {{ subscriber.current_provider }} is working out for you. Since we first spoke a few years ago we have been investing a lot in improving our service and, due to those improvements, a lot of businesses are finding that we are a better fit for them now.

If you’re really happy with {{ subscriber.current_provider }} then great. If not, I would love to talk with you for a few minutes to see if we might be a better solution for you today.


{{ from_name }}

Implementation in Drip

Create the “Lost Deal Campaign” with these three emails.

Lost deal drip email campaign

(If you use a CRM system to track emails you have sent to your leads set the campaign up to automatically BCC yourself on each email so that it will be picked up by your CRM.)

Create a new workflow:

Lost deal workflow in Drip

  • Start workflow then the tag “not_interested” is applied.
  • If the subscriber has a custom field set with the current provider (the emails you created reference that so you don’t want to send them without that information) then send campaign otherwise exit workflow.
  • Wait ten months to start the email campaign
  • Create a goal (“customer” tag applied) so that if that happens the subscriber is pulled from the “Lost Deal Campaign” and not sent anymore of those emails.
  • I have a separate workflow (“Customer Onboarding”) which is triggered when the “customer” tag is applied.

One obvious improvement is to add a campaign that doesn’t reference the current provider so that all lost deals get follow up even if you didn’t get the information about which of your competitors they use.

When creating a subscriber in Drip (Import/Bulk Ops -> New Bulk Operation -> Enter a list of email addresses) you have to create them using an email address and then you can go in and update their fields. Be sure to set the “current_provider” customer field prior to adding the “not_interested” tag. to Drip

If you’re using CRM software then you probably would prefer to automate this whole process–more time for sales! You can do that using Zapier so that when you mark a lead as “Not Interested” in your CRM (or opportunity as ‘Closed: Lost’) it will automatically create a subscriber in Drip, set their current provider, apply the ‘not_interested’ tag, and start sending them the email campaign in 300 days.

I use and this is the zap I created for this:

Lost deal email Zap with and Drip

The trigger: trigger in Zapier

The filter for only status changes to ‘Not Interested’:

Zapier filter for lost deals

Setting up the contact in Drip:

Adding contact to Drip in Zapier

(edit: If you use Zapier to create subscribers from contacts then you don’t currently get separate fields for first and last name but rather a full name field. You can use the following in your Drip emails in order to address your emails to someone’s first name: “{{ | split: ‘ ‘ | first | capitalize }}”. Thanks to Andy at Drip for that.)

“No” means “not right now”

You put a lot of work into turning leads into customers. Don’t let the “no” be the end of your relationship. By using this lost deal drip email campaign you turn that “no” into just one step of a much longer relationship. One that hopefully includes them becoming a customer at a later date.

Email Template Roundup

I am all about engaging people for your business through email. (Literally that is what my book is about.) Throughout your relationships with your customers, prospective customers, and industry peers there are countless opportunities to reach out to someone and to push your relationship forward.

The problem with having so many opportunities is that it takes a long time to create all of those emails. Writing (and revising) a great email sequence takes time so to get a head start you can use email templates that sales and marketing masterminds have shared with us.

I have used each of the templates in this roundup in one of my businesses.

Educational Campaign Emails

Providing value to someone upfront is one of the best ways to turn them into a prospective customer. A great way to do that is to teach them something related to the product or service you sell. For example Home Depot does a workshop where they go over a different home repair each week. You can do the same via a webinar. However, an easier, and scalable, way is to create an email course around a topic.

The email marketing software Drip comes with a couple templates already set up for that: the “5-Day Email Mini Course” and the “4-Week Email Mini Course”. I like the daily course better for teaching a specific topic with the weekly course more when you are presenting more general content about your industry.

This is the first email:

Thanks for checking out my 5-day crash course on **TOPIC OF COURSE**

I’m **NAME**, the founder of **COMPANY**. My goal for this course is to provide you with new techniques and approaches for **MAIN BENEFIT OF THE COURSE**, while keeping them as actionable and succinct as possible.

And today, we start with a look at **TOPIC OF TODAY’S EMAIL**.


This email course will provide you with actionable tips on how you can **BENEFIT OF THE COURSE**. More on that later…

Tomorrow, we’ll be delving into **TOPIC OF TOMORROW’S EMAIL**.

If you have any questions in the meantime, please hit the reply button and drop me a line. I will respond personally to every email.

And if you’re ahead of the curve and want to get started, feel free to learn more about **PRODUCT_NAME** here.
Until tomorrow,


Other email campaign blueprints they have are:

  • Follow-up (Post-Demo)
  • Follow-up (Sample Report)
  • Follow-Up (Subscription Trial)
  • Cart Abandonment Recovery

WIth their workflow feature it is easy to guide a customer through multiple email campaigns from the time they are a prospect to when they become a customer and to later upsell them based on their usage. Great for all businesses but particularly for SaaS businesses.

Sales Emails

Steli Efti of has become something of a motivational speaker for startups. You listen to him give a talk and come out of it knowing that you can take the leap today and start selling. Key to his method are to stop procrastinating and to just start sending the emails, making the calls, and to never stop following up.

This simple cold email (his example is selling Dropbox to a law firm) can be modified for any software or service industry:

Hi [contact.fist_name],

My name is [user.first_name] with [].

We help law firms store & manage all of their client data securely in the cloud. I wanted to learn how you handle data storage at [lead.display_name] and show you what we’re working on.

Are you available for a quick call tomorrow afternoon?

A great takeaway from the follow up emails is that you offer the lead a few specific times for a possible call:

Do you have a few minutes for a quick call later this week?

Wed @ 11 am PST
Thur @ 2 pm PST
Fri @ 3 pm PST

If you ask them to make the first move in scheduling a time you’re often going to wind up waiting indefinitely. Present them with a few times they can say yes or no to. If they come back saying that none will work then try three new times. And keep following up until you get that call scheduled!

A few more templates from that I use can be found here.

Customer Onboarding Emails

I love the “You’re In” Email from Groove as the first email in an onboarding sequence. I feel this one can be modified for use whether you are selling a product or a service. You’re engaging your new customer to learn a little bit about why they choose you which is very helpful when creating your customer profiles.

I really appreciate you joining us at Groove, and I know you’ll love it when you see how easy it is to deliver awesome, personal support to every customer.

We built Groove to help small businesses grow, and I hope that we can achieve that for you.

If you wouldn’t mind, I’d love it if you answered one quick question: why did you sign up for Groove?

I’m asking because knowing what made you sign up is really helpful for us in making sure that we’re delivering on what our users want. Just hit ‘reply’ and let me know’

By the way, over the next couple of weeks, we’ll be sending you a few more emails to help you deliver awesome support to your customers. We’ll be sharing some tips, checking in with you and showing you how some of our customers use Groove to grow their businesses.

I now use the “hit reply and let me know a little about you and/or your business” in most of my email campaigns. Not everybody responds but you learn so much when they do.

This sequence of onboarding emails from Baremetrics is great for SaaS companies to use throughout a trial period. Days 1,2,3,5, 12, and 14 specifically. Some of the other days are pretty specific to their app. I also hesitate as it is a lot of emails over a two week period of time but you can check open, click through, and response rates and find what works best for your business.

Failed Payment (Dunning) Emails

This one is for SaaS or other businesses that bill a customer’s credit card monthly.

Patrick McKenzie (Patio11 on the Internet) gave a talk at MicroConf Europe 2013 titled, “Building Things To Help Sell The Things You Build”. In it he brought up “dunning emails” which are the emails that a user receives when their credit card charge fails which usually happens when somebody gets a new card but forgets to update their billing information.

He brings up the point that when a charge fails the language in the notification email needs to be gentle. Use terms like “pausing your service” rather than “cancelling your account”. From Christoph Engelhardt’s notes on Patrick’s talk:

  • Everyone gets 3 dunning emails
  • Get to the point ASAP
  • Prominent link to capture updated CC data
  • Extend a 3 day grace period, try daily within grace
  • Don’t forget a “You didn’t update so we took the liberty of pausing your account” email

This post by Richard Felix shows what Drip itself does with their dunning emails. They use a series of three emails as Patrick recommended. You can see from the first email in the sequence that they don’t place any blame on the user (the card might have expired), use language that puts the blame on Drip (“will let you know if it’s still not working”), and don’t mention the possibility of disabling the account until the second to last sentence.

From: Rob at Drip
Subject: Uh oh, credit card fail – your emails will stop sending soon…


It appears we’ve run into a problem charging your credit card on file at We’d love to keep sending emails to your subscribers – so let’s get you back on track!

The most common two causes of card rejections are that your card has expired, or that your bank has rejected the charge.

So first, visit your billing settings to double check that your card has not expired (and just for kicks, go ahead and update it to see if that fixes things). We will attempt to charge again in 48 hours and will let you know if it’s still not working.

If you hear from us again about this, the most likely explanation is that your credit card company is rejecting our charge. Please call the number on the back of your card and ask them to allow charges from moving forward.

As of now your account is still active, but it will be disabled if we aren’t able to get your card working. So let’s get your account back on track and serving up more tasty email goodness!

The Drip Team

Networking (Influencer Outreach) Emails

A quote I love from Charlie “Tremendous” Jones (a motivational speaker) is:

“You will be the same person in five years as you are today except for the people you meet and the books you read.”

Networking is a great way to learn and grow both your business and as a person. For many people it requires stepping outside of your comfort zone and reaching out to people with more experience than you and whom you respect.

I recommend creating a plan to reach out to ten people a month that you follow on Twitter, read their blog, heard them on a podcast, or are in your network on LinkedIn (or are one removed and you can ask somebody you know for an introduction). When you have a list of ten people for the month then drop them an email.

Number two and three of Groove’s email templates (they really do share a lot of great content) are emails you can use to reach out to influencers in your industry or people in your network (look at their profile for articles they have written, organizations they are a part of, and charities they support):

Hi [firstname],

I loved your post about [subject + authentic reason].

I wrote a post about [compelling teaser]. I know you’re an expert on this, and I’d really appreciate your feedback.

Do you mind if I send you a link?

[your name]

The Underdog Action Plan

Use one of these templates to create a new campaign of at least three emails for one of these stages of the customer relationship:

  • Subscriber
  • Prospect
  • New customer
  • At-risk customer (somebody who is paying for your product/service but isn’t using it)

If you are struggling for ideas just drop me an email (will at the domain) and I’ll help you brainstorm.

Remember, at the end of the day, the more great content you have created the more you will be able to engage your audience and convert them into happy customers.

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Guide to creating customer profiles

People respond much better to targeted marketing than they do to general marketing. Imagine being able to talk to each potential customer directly! We’re a little ways from that but with a combination of tracking, big data, and A.I. improvements I think the future is hyper-targeted marketing.


Until that utopian future (if you are a marketer) or dystopian future (if you don’t like being marketed to) we will have to settle for other methods to target our marketing messages and customer onboarding processes. In order to do that you need to be able to effectively segment your customers in order to tailor your message.

The upside to creating a series of customer profiles (also known as buyer personas) is that your blog content, mailing list emails, and ads will convert better. This is particularly helpful if you place ads on Facebook. The downside is that creating separate content for each segment is a lot more work. But it is work that will pay off in the end.

Customer profile details

For creating profiles I like this character development outline that I used in my college playwriting class. It is called Character Bone Structure and is from Lajos Egri’s The Art of Dramatic Writing. I’ve used it not just for creative writing but for creating buyer personas for my marketing efforts.


  1. Sex
  2. Age
  3. Height and weight
  4. Color of hair, eyes, skin
  5. Posture
  6. Appearance: good-looking, over- or underweight, clean, neat,
    pleasant, untidy. Shape of head, face, limbs.
  7. Defects: deformities, abnormalities, birthmarks. Diseases.
  8. Heredity


  1. Class: lower, middle, upper.
  2. Occupation: type of work, hours of work, income, condition of
    work, union or nonunion, attitude toward organization,
    suitability for work.
  3. Education: amount, kind of schools, marks, favorite subjects,
    poorest subjects, aptitudes.
  4. Home life: parents living, earning power, orphan, parents
    separated or divorced, parents’ habits, parents’ mental
    development, parents’ vices, neglect. Character’s marital
  5. Religion
  6. Race, nationality
  7. Place in community: leader among friends, clubs, sports.
  8. Political affiliations
  9. Amusements, hobbies: books, newspapers, magazines he reads.


  1. Sex life, moral standards
  2. Personal premise, ambition
  3. Frustrations, chief disappointments
  4. Temperament: choleric, easygoing, pessimistic, optimistic
  5. Attitude toward life: resigned, militant, defeatist.
  6. Complexes: obsessions, inhibitions, superstitions, phobias.
  7. Extrovert, introvert, ambivert
  8. Abilities: languages, talents.
  9. Qualities: imagination, judgment, taste, poise.
  10. I.Q.

(You can bet the door-to-door salesmen of yesteryear would attempt to learn these about a customer within moments of the door opening.)

Obviously this goes into a great deal of detail and some of it you definitely don’t need (but let the data tell you what you need and don’t!). You can probably make things a bit simpler to start with. If you are targeting consumers you can start by using the following four variables or even less:

  • Gender
  • Age (brackets of ten years)
  • Marital status
  • Income

2 options for gender * 5 options for age (20s, 30s, 40s, 50s, over 60) * 2 options for marital status * 2 options for income (keep it simple with over/under an income figures such as $50,000) = 40 different possible customer profiles.

You can see that the more variables you use vastly increase the number of profiles. So, start with just a few variables that you deem important and work from there. And don’t be afraid to repurpose content or create content that spans profiles. Depending on your product somebody married in their 30s is not going to be all that different from somebody married in their 40s.

When selling to small businesses a few simple variables to start with might be:

  • Industry
  • Role (owner or employee)
  • Revenue

This is not a substitution for picking up the phone and talking to customers. The more you talk to and engage your potential customers the more you will learn about them. Whenever you are in doubt about something in your business talking to customers will go a long way towards helping you find an answer

Creating customer profiles

Here are a few steps to help you being filling in your customer profiles:

1. Identify the data you already have

You might already have some data on your customers but might not know it. If you use a CRM system for sales it likely has some data in there about your customers. (If it doesn’t you should definitely add some custom fields in order to start recording things such as company size, industry, current solutions they use, and any personal details about your contact that they mention.)

Where you definitely have some hidden data is in your email. Most business people use email signatures which typically contain a few good pieces of information you can use. Here are a few things you can probably glean from a signature and then supplement by looking them up on LinkedIn (a great task for a virtual assistant):

Creating customer profiles from email signatures

2. Go to where your customers hangout

Facebook groups, LinkedIn groups, and Twitter are all places you can look at to find people talking about the problem that your product or service solves. Look at the discussions they are having and the people that are having them. You should be able to fairly quickly identify a few buckets that your potential customers fall into.

As an experiment (the Underdog Action Plan for the week) create and write down three basic profiles and then try to put twenty people into the bucket that you think best fits them. You’ll probably get most of them, particularly if you did early customer development, but you also might find that the most vocal people online are not potential customers but just people with too much time on their hands. Reach out to the twenty people you assigned to a bucket and see if you can ask them a few questions.

Pro tip: 44% of U.S. consumers go straight to Amazon to search about products. Read the reviews people leave on books and products related to your industry to learn about your potential customers.

3. Ask your customers directly

It is always best to pick up the phone and talk with a customer directly. However you can also leverage technology to get their feedback at various points throughout your relationship such as when they visit your website (I’m sure you have been asked to fill out a survey on a website), when they become a customer, and later after they have used your product or service. This is an example for a questionaire for a new customer.

Using Google Forms you can easily create a customer feedback form and ask them to fill it out. From “Start a New Form” select the “Customer Feedback” form. You might need to click on “More” in which case you will find it listed under the “Work” forms.

Click on the “Feedback Type” question and then click on the trashcan to delete it. Now click on the “Name” field followed by the plus icon on the right. Add in questions about the customer that you can use to create profiles:

Google Forms Customer Profile
Don’t add too many or you risk people not responding. Ideally it should take somebody just a minute or two to answer all of the questions.

After you have finished click on “Send” in the upper right and then click on the paperclip icon to get a link to send to your new customers. As the results come in you can view them from inside forms or, even better, view the data in Google Sheets so that you can analyze it.

Customize and convert

Knowing somebody’s background and ambitions can really change the language you use when describing your value proposition. Appealing to your customer’s interests is imperative to generating sales. It is going to require experimentation and learning to do so will be the key to your growth engine.

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Selling to a Cold Lead

Selling to a cold lead

At some point many businesses, and most professional service businesses, will go through a phase where they try cold outreach to generate new business. Traditionally that was cold calls and direct mailings but now often takes the form of cold emails (not to mention the blind Twitter follow). It is a law of the universe that these methods don’t convert as well as warm, inbound leads but when you’re looking to grow sales you will try anything.

There are methods for increasing the odds so that your outbound sales efforts go from feeling futile to being a repeatable source of new business.

Identifying customers to target

Obviously the first step towards cold leads becoming a viable sales channel for you is finding a good source for them. The easiest, but lowest quality, source would be to buy a list of leads. Those tend to be sold many times so the people on them receive a lot of sales calls already and are even more predisposed to ignoring you. They also come with none of the background information that is helpful in making a sale.

A better, but much more time-consuming, avenue is to manually source the leads yourself. My main method of doing so is Google searches. Every month I spend about four hours on a weekend watching movies and adding to my list of people to contact. “CPA Chicago”, “CPA Memphis”, etc. I go through about ten pages of results and manually copy the contact information into a Google Sheet. It is a lot of work but I end up with a list of people actively practicing their profession and can also make note of items of interest on their website or in their bio that I can include when emailing them. Those can be:

  • Blog posts they have written
  • Newspaper articles that have quoted them
  • Conferences they have spoken at
  • Whitepapers
  • Industry accolades
  • Where they went to school
  • Interests

Including one of those in your email shows that you spent a little time researching them, that your email is personalized and not just spam, and that you appreciate them as an authority (they have worked hard to get where they are and like that to be acknowledged).

Even better than Google searches is going to where your potential customers hang out online (forums, Reddit, industry publications) and identifying them there.

You don’t want to target just any person at a company. You want to target the person who is most acutely aware of the problem that your product or service solves. If you sell time-off management software you would want to target HR. Expense reporting software you want to target accounting. When in doubt, and you’ve qualified the company as a good candidate, target the owner.

You want to target the person who is most acutely aware of the problem that your product or service solves.

Before every cold call write a cold email

My favorite tactic to warm up a lead before cold calling them is to send them an email. It doesn’t turn them into a warm lead but makes them a slightly warmer lead. When you get then on the phone, or you leave them a voicemail, you are able to reference a previous communication. Instead of just saying, “not interested” they are more likely to say, “oh yeah, I saw that email.” They will be more likely to let you start a conversation with them.

One of my templates:

Hi <first name>,

I’m reaching out to you because you are the <job title> of <company name> and think you might be the person to talk to about <the problem your product or service solves>. I would love to ask you a couple of questions about how you currently <deal with the problem> to see if it is something we might be able to help with.

Do you have a few minutes for a quick chat?

Monday at 10:30 am EST
Tuesday at 2 pm EST

Thank you for your time and I look forward to talking with you.


Sometimes you might want to give an extra push with your cold emails. For small businesses one tactic is to appeal to the owner’s growth goals while recognizing their cash flow fears (every small business owner has them).

When you are growing your business every dollar counts so it is good to get <some software or service> to handle <the problem> before you have to hire for it. This way you can keep dedicating resources to your core business while keeping <people from having the problem>.

End your cold email with the assumption that you are going to talk with your lead at some point. “Looking forward to connecting with you” subtly pushes them a nudge further down the funnel as more correspondence, and a phone call, is now a forgone conclusion. “I can’t wait to talk with you and see if we might be able to help <with your problem>.”

Tracking email opens

Knowing whether or not a lead has opened an email influences my follow up course of action. If I have sent somebody an email but it wasn’t opened then I might try again a week or two later with a slightly different email and different subject line. (Some people disable read receipts so you don’t want to send the exact same email.) If they don’t open the second email, but I really think they would be a great customer, then I try a phone call. If I have no reason to believe they are any different that any other prospect then I assume they aren’t interested right now and mark them for another follow up six months out.

If somebody has opened my email, but hasn’t responded, I call them a few days later. This way my email is still fresh enough in their mind that they remember receiving it and have maybe given a few moments of thought to possibly doing something about the problem that I can solve for them.

If you are sending your email through a CRM then it should have built-in open tracking. If you are using Outlook it has read receipts built in (though a lot of people don’t respond to them). Boomerang for Gmail also offers them among many other power email features.

The sales call

Every business believes it is unique

If you get your lead on the phone when you call start by introducing yourself and mention that you are following up on the email. My two biggest tips for the rest of the phone call are:

  • Make the conversation about them
  • Use the language they use

The best way to make the conversation about your customer is to ask questions:

  • How do you currently handle <the problem>?
  • What is one aspect of that process that works the best?
  • What is one thing you would change if you could?
  • Are you using any products or services <for this problem> currently?

These questions get them talking. Shut up and listen. When they stop talking ask another question. What you learn now helps you frame your solution as the answer to their specific problem. Use the word “you” instead of “I” or “we”.

Learning the language of your customers and the industry jargon helps to show that you understand the unique problems their business faces. Every business believes it is unique but you greatly increase your chances of making a sale if you make them believe that you have a background in their industry or have more than a casual understanding of it.

After you have asked them some initial questions you are then prepared to address them mentioning an aspect of how your product or service can help them. You are not giving an elevator pitch. You are learning about their problems and brainstorming ways to help them.

How and when to ask for a close depends a lot on what your product or service is and the price point. If it is low-priced and it easy to implement then you can ask if they are interested and immediately follow it by asking what it will take to make the sale. On the other hand, if you product is high-priced, complicated or time-consuming to implement, or would be part of one of their vital business functions then this is likely one of many phone calls, demos, and proposals you make. Your goal of this call is to schedule a second call.

If you initially only asked for a few minutes of their time then it is okay to ask if they have a few more minutes or if they would like you to send them some more information. Schedule a follow up call with them right then.

Things to not do on the sales call

The first thing to not do on a sales call is to be unprepared. It is important to be prepared and be in the right state of mind before picking up the phone:

  • Be able to pronounce the lead’s name and look up their company on Google or LinkedIn so that you aren’t totally oblivious about their company (they spend at least eight hours a day working towards something and you can do them the courtesy of knowing what that is).
  • Have an answer for each of the most common objections you hear.
  • Do whatever is needed in order to get your mind and emotions ready for sales. It is often advised to put on a song that pumps you up or do some pushups. If you are having a bad day then skip the sales calls entirely. Work on something else (maybe building the lead list) and come back to the calls tomorrow.

Don’t be too direct with the qualifying questions on the initial call. When I receive a sales call and somebody asks me “how many employees do you have?” or “what is your annual revenue?” then my initial reaction is “that is none of your business”. That also suggests that they haven’t done any homework and that I am no more than a line on a spreadsheet for them.

The question that really gets to me the most is when somebody asks, “What is your budget?”. No! My thought is, “Tell me your price and let me decide if it is worth discussing further. You’re the one who called me! I know that the first one to name a number loses.”

Those are all alright questions for a second call but for the the first call they evoke the feeling of browsing on a car lot and being approached by the salesman.

Finally, throughout your life you have heard the advice, “don’t take no for an answer.” However when you are selling a definitive “no” is the second best thing you can hear after a “yes”. Embrace the no and move on to another lead.

The voicemail message

Often you don’t get the person on the phone and have to leave a voicemail. Always start and end by saying the person’s name:

“Hi <first name>”

Following the greeting I introduce myself:

“This is Will from Engage Tactics”

And remind them about the email I sent them:

“I’m following up on an email I sent you on <day of week>”

Then the meat of the call in no more than two or three sentences:

“As I said in the email, I’m hoping to ask you a couple of questions about <the problem> and how you are currently dealing with it. We <have the solution> and I would love to talk with you for just a few minutes to see if it might be a good fit.”

Your information so they can call you back (say this slowly so that they have time to write it down):

I look forward to talking with you. My number is (555) 555-5555. Again this is Will from Engage Tactics and my number is (555) 555-5555.”

And then follow that up with my ending where I again use their name:

“Thanks <first name>. Have a great day.”

Follow up

The follow up is one of the most critical parts of the sales process. People have a lot on their plate and they are always going to address the fires in front of them before investing time with you in order to keep those fires from starting in the first place. Short term needs trump long term goals. It is up to you to remind them that your product or service can start helping them (nearly) immediately.

Every phone call you have, even the ones where they say no, should have a follow up email. Go over what you talked about and what the outcome of the conversation was. Thank them again for their time. Mention that you look forward to talking with them again. Send a calendar invite if you scheduled a follow up call.

If they say no then still send a follow up email that thanks them for taking the time to talk with you and say, “if you change your mind and would like to talk again about <problem> and <your solution> my contact information is below.”

Emails also need to be followed up on. If you sent an email request for a phone call and didn’t get a response then wait a week and send another request. Then do that again. Every lead should be contacted a minimum of three times before you move on. I would estimate that a third to half of my leads that have responded did not respond to the first email.

Document everything

Cold calling is hard work but builds character.

The key to getting a cold lead sales process to work is to make a record of each communication. You can use one of the many CRMs out there to track all of this (I particularly like for outbound sales) or even use a free tool like Trello with a card for each prospect. Just make sure that you can always look up where in the funnel each lead is, when you called or emailed them, and what the outcome of any conversation was.

Secondly, when you find that you are getting some traction with your sales process then document it. In a Google sheet, an Asana project, or somewhere else, list each step of the process with extreme detail. By doing this you will be able to hire people to handle different parts of the process for you. If you know you can turn x leads into y dollars and that paying somebody to find you x leads (with your documented process) costs less than $y then you have created a sustainable sales channel.

Cold selling is hard work but builds character and is one of the best ways to learn more about your customers and how you should frame your solution to them across all of your sales channels.

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