Sales Storytelling for Startups

Photo by Priscilla Du Preez on Unsplash.

Selling has Changed:

Today, thanks to the internet, buyers are empowered and sales teams must adjust. At the end of the day, sales people still need to nurture prospects, close deals, and hit quotas.

I recently gave a talk for the Sales & Marketing Meetup at WeWork Kurfürstendamm in Berlin, where I shared some essential sales storytelling tips plus examined how to weave story into sales tech for startup founders and scale-up leaders looking to improve sales enablement with digital tools. Since these are common challenges that startups and scale-ups face, here’s a brief recap so you too can benefit from what was shared.

Table of Contents:
Act One — Introduction to storytelling:

* Storytelling Framework
* Build your Business on a Story Foundation
* Storytelling is a Superb Tool for Startup Founders
Act Two — How to craft a sales story:
* Buyer Personas
* Customer Journey
* Funnels vs Flywheels
* Jobs Theory
* Mapping a Go-to-Market Sales Strategy
* Writing a Sales Proposal with Story
Act Three — Integrating sales story with sales technology:
* Basic CRM software
* Email Tracking and Proposal Attachments
* CRM Deal Pipeline
* Delighting with Customizable Invoices

Introduction to Storytelling:

Storytelling is the ultimate competitive advantage because it helps customers understand the benefits of using your products, ideas or services.

Story works because the human brain is drawn towards clarity and not confusion. Story is a sense-making device. It’s a powerful tool for organizing information.

Story works across platforms:
*Still Pictures
*Social Media
*Sound (radio, podcasts)

Storytelling Framework:

Most stories happen in three acts: a beginning, a middle and an end. Characters are introduced and the scene is set in the beginning — sometimes referred to as Act One. Think of it as ‘the status quo’. A typical story starts with the hero wanting something and the question becomes: will the hero get what they want? This is similar to your customer with a problem they need solved!

Next in the middle, or during Act Two, the main character faces a conflict that must be overcome. This is where the main character’s world is turned upside down and they must overcome a series of obstacles to achieve their goal. Replace ‘character’ with ‘my customer’. It’s important to define something here that your customer wants or needs, because as soon as we define this, we place an age old story question in their minds: Can this brand really help me get what I want?

In the end or Act Three, the story resolves. In a traditional story the hero conquers the villain and makes the world a better place. In your story this translates to your customer conquering their ‘problem’ and their life is made better because of your product, service or idea!

Photo by Startaê Team on Unsplash.

Questions good storytelling answers include:

1. What does the hero want?

2. Who or what is opposing the hero getting what s/he wants?

3. What will the hero’s life look like if s/he does (or doesn’t) get what s/he wants?

Build your business on a story foundation:

Storytelling is a Superb Tool for Startup Founders:’s Co-Founder captivating the crowd at GTEC’s Demo Day in Berlin.

Storytelling is a critical part of building a brand. Founders often try hard by focusing heavily on small details when they explain features or technologies. This information can be valid, however, it isn’t easy or engaging to follow.

Without a clear sense of purpose, pitches can quickly become boring, uninspiring and easy to forget. If founders can deliver a clear brand narrative, it has the power to increase the value of a business’s product or service.

Founders looking to launch or scale should implement a strategic storytelling practice throughout their business. Here are four reasons why:

  1. The backbone of a strong sales and marketing strategy is always a clearly communicated story.
  2. Heartfelt storytelling is both human and profitable.
  3. Stories emotionally connect people and create brand loyalty.
  4. The right brand narrative has the power to increase the value of a business’s product or service.

*Warning: Founders often focus heavily on fine details like features or technologies. While this information can be valid, it is not easy or engaging to follow. Without a clear sense of purpose, pitches become boring, uninspiring and easy to forget.

Buyer Personas help you clarify your customer:

To research your buyer personas, find a mix of people to speak with:

  • Existing customer base is the perfect place to start interviews
  • Reach out to both “good” and “bad” customers
  • Balance out your interviews with people who have not purchased your product or know much about your company
  • Leverage your network to get referrals for people who may fit into your target personas, particularly if you’re heading into new markets or don’t have any leads or customers yet
Buyer Persona Example

Having a deep understanding of your buyer persona(s) is critical to driving:
*content creation.
*product development.
*sales follow-up.
*and really anything that relates to customer acquisition and retention.

Buyer Persona Example

Share what you’ve learned about Persona motivations:
*What keeps your persona up at night?
*Who do they want to be?
*Most importantly, tie that all together by telling people how your company can help them.

Note: If you’re struggling to research and write your ideal buyer personas, there are many free tools available online. HubSpot’s free buyer persona generator is one of the best I’ve seen, and it does walk you through the task step by step. Download it here.

Generate your buyer personas with this free tool.

Understand your customer’s journey:

Typical Sales Funnel

A flywheel is a mechanical device specifically designed to efficiently store rotational energy. Where things fall out the bottom of a funnel, a flywheel doesn’t lose anything but instead uses everything for energy. The amount of energy stored in a flywheel is proportional to its rotational speed.

In a sales and marketing context, flywheels represent a circular process where customers feed growth. If you look at the flywheel diagram below, you can see that your sales process needs to solve problems for prospects in each stage: attract, engage, and delight. This keeps your flywheel moving.

Three factors dictate how much momentum your flywheel contains:
*How fast you spin it
*How much friction it has
*How it’s composed — how big it is and how much it weighs
The best teams will have strategies for all three.

HubSpot’s Flywheel Graphic

Attracting is about using your expertise to create content and conversations that start meaningful relationships with the right people.

Engaging is about building lasting relationships with people by providing insights and solutions that align with their roadblocks and goals.

Delighting is about providing an outstanding experience that adds real value, empowers people to reach their goals, and become promoters of your company.

Extra Reading — Jobs Theory:

Competing Against Luck book

Harvard Business School Professor Clayton Christensen’s discovered a theory that explains your customer’s reason for buying from you. The theory is based on the notion that people buy products and services to get a “job” done.

Jobs-to-be-Done theory is best defined as a group of principles that explain how to make marketing more effective and innovation more predictable by focusing on the customer’s job-to-be-done.

Christensen’s research will help you better tell your buyer persona sales story. For example, McDonald’s hired the Harvard Professor to find out why they were selling milkshakes for about 90 minutes early in the morning while sales were minimal throughout the rest of the day.

Christensen and his research team decided to interview people coming out of McDonald’s with their orders. They asked people who purchased milkshakes why they bought them. It turns out milkshakes were in fact being used as a breakfast substitute by the early morning customers. This meant it was competing against other breakfast foods. But was there any other job it was also doing that make it a better choice than a banana or doughnut?

The research team discovered that customers who purchased early morning milkshakes had long morning commutes to work driving in their car. They needed a food that could be eaten using one hand (like a banana or doughnut) but also something that would last for a portion of the boring ride, so the driver would have something else to do. A-HA moment!

Once McDonald’s understood the full job that needed to be done, they were able to offer customers better morning milkshakes and in doing so, they increased sales.

Harvard Professor Clayton Christensen giving a guest lecture on ‘Jobs Theory’.

Understanding what job your customer is hiring your product or service to do will help you better produce and package your offering. Persona stories should include what job you’re doing for each persona.

Quick sales storytelling hack:
Learn what’s interesting, validate it and then lead with it.

Warning: a common storytelling mistake startups make is bypassing the problem and diving straight into the solution.

Mapping your go-to-market sales strategy:

Attract process for SaaS example:
In this example, I’m using the above inbound marketing principles to get the flywheel spinning.

For example, to provide value before you extract value, you can invest in creating free content through things like blogs, webinars, ebooks, social media, video lessons and so on.

These content items should address ‘problems’ or ‘jobs’ your buyer personas have.

Engage process for SaaS Example:
To make it easy for prospects to engage with your product and potentially purchase them, you could offer trials or free versions, so users can try before they buy and seamlessly upgrade.

For SaaS products, free trials help onramp customers onto a qualified path. Depending on the product’s cost, some free trial users might be ready for sales while others on a lower cost item, may require more nurturing from marketing, like via emails, before they’re ready for sales to convert them.

A classic example of this is Microsoft Office free trials for business. When a prospect enters a free trial, they are not sales qualified yet. They remain with marketing. However, once a prospect asks for an extension and enters their credit card number to continue using for another free month — they now become sales qualified.

Delight process for SaaS Example:
You can help your customers succeed (and retain them!) through a mix of guided and self-service education for your product or service.

Another example, you can also give paying customers access to a core implementation and strategy team, free users are offered light-touch free support, and both groups are given access to extensive user guides and knowledge base documentation.

Here’s a snapshot of what the above looks like in a graphic:

Important!: You’ve worked so hard and invested money to attract, retain, and delight. Don’t forget to measure customer success! By reviewing your success you’ll have a better idea of what works, and where you need to make improvements for more success.

Here are some sample ways to measure the SaaS example above:
Attract: Topline metric here could be monthly website traffic. Measure how much traffic you gain month-over-month.

Engage: This SaaS example flywheel moves visitors through the “Engage” stage in two steps:

  • Focus on how many free users of your product enter the flywheel each month. Measure how many of those users churn. The more free users that you have the better momentum it can generate.
  • Build upgrade points in your product where free users can become qualified sales leads. Track how many of those qualified leads close into paying customers, and then track how many of these churn. Each churn causes you to lose momentum.

If you need some inspiration to help put all of this together into an actionable plan, use a free Sales Plan Generator to walk you through each stage of the plan. A sales plan is an actionable way to simplify and document your sales goals and strategies to accomplish them. Budgets, marketing strategy, positioning, and other topics are also explained.

Your lead is ready to buy — proposal time!:

Want to increase your close rate?
1. Only sent proposals to *QUALIFIED* leads
2. Digitize the process to speed-up and track progress

For example, when a lead fills out a form requesting a quote, instead of sending your proposal straight away — your sales rep can reply sending additional information like an ebook or video asking the prospect to read or watch before the quote is issued. You’ll have some drop-off, but you will know the ones that read or watch are serious, and you’ll close sent proposals at a higher rate.

Have a repeatable process to make things easier. Automate what you can to do less work while you’re closing deals faster.

Include a strong email signature:

Email Signature Generator

With this free email signature generator, you can include everything from your phone number, to your photo and even your certifications to help make a powerful professional first impression.

Start by filling out the form to populate your signature, then click across to the ‘social’ and ‘style’ tabs to add your social media links and customize your design. When complete, click the ‘create signature’ button for several export options — and you’re done! Then simply add it to Gmail, Outlook, Apple Mail, Yahoo Mail, or any other email provider.

Sample Sales Proposal Content:

Proposal Cover Example

Sections to include:
*Cover Page
*Executive Summary
*Goals and Challenges
*Deliverables / Approach
*Scope of Work / Timeframe
*Success Metrics
*Customer Testimonials
*Breakdown of the Budget

*Include the ability to use a digital signature for a faster sign-off!
*T&Cs / Contract: send these with the proposal, not separate, to get a unified sign-off without the chance of confusion or delay by sending a proposal first and your terms after they accept the price.

And finally, don’t forget to include an explaination of the next steps! Either in your email introduction or in your proposal document around the signature page — be sure to guide your customer — tell them where to sign and then what happens after they sign. For example, a copy of the signed contract will be emailed to them plus Sally from your team will call Dan in their team to organize the project kickoff.

Integrating sales story and sales tech:

Using a basic CRM for sales enablement:

Marketing Automation:
Primarily used to attract and convert leads as well as help produce sales opportunities. This tool is used by marketers primarily.

NOTE: Both tools should work together just like marketers and salespeople should work together.

HubSpot CRM contact page view.

Now that you’ve written your proposal to speak to your customer’s pains or jobs to be done, it is ready to be sent.

But since 60% of proposals land in the ‘valley of death’ you’ll want to know how your proposal is moving along once you send it:

  1. Has your email been opened?

2. Has your email been forwarded? Is there’s another decision maker???

3. Provide for digital signatures for faster sign-off.

A strong free CRM that helps people who need to sell close more deals while doing less work is HubSpot CRM. People who need to sell can email prospects with detailed signatures and even attach a proposal document to the email from inside the free HubSpot CRM. Emails are tracked so you’ll know when a prospect opens your email. With HubSpot CRM your entire sales pipeline is also always visible.

Example of HubSpot CRM’s Deal Pipeline view.
  • See your entire sales funnel on a clean, visual dashboard. Sort deals won or lost. View your scheduled appointments and contracts emailed. You can also measure your performance against quotas you’ve already set. It’s also possible to sort deals by name, owner, amount, or even stage with custom filters for actionable insights.
  • HubSpot CRM automatically tracks interactions with your customer from email, across social media, and on calls.
  • Save time by never needing to search through your inbox and spreadsheets to figure out where a prospect is at. Instead, see every interaction with a lead in a tidy timeline, including calls, emails, meetings, and notes in the HubSpot CRM.

Don’t forget to delight!:

An invoice, or sales invoice, is a billing document issued by a seller to a customer. The document typically includes:

Invoice Template Generator
  • Details contact and billing information
  • Quantifies an itemized list of goods or services sold
  • Provides a clear purchase total
  • Defines any discounts
  • Contains a unique invoice number and date
  • Outlines any payment details or a due date if necessary

Your invoice details will change slightly depending on whether you are providing a service or a product (e.g., billable hours and rate vs. quantity and cost).

Using invoice templates and can help ensure best practices for creating a professional invoice are followed, especially if you are new to billing clients. This free invoice template generator provides 10 different fully customizable styles to get you closer to having revenue flow into your bank account.

And finally, I’m a HubSpot Certified partner. If you’d like to try HubSpot’s Marketing Software for free for 30 days, you can get your free trial via this link. HubSpot’s Marketing Software includes everything available on the free package plus features like marketing automation, SEO, blogging tools, and landing pages. Please note, if you upgrade and pay I might get a commission in some circumstances.

Cambridge MBA | Marketing Consultant | Speaker | Author | Ghostwriter
Follow me on Medium and Twitter @CambridgeTricia
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Marketing Executive combining Storytelling & Digitial Technology. Techstars Mentor. Former Bloomberg Journalist. Cambridge MBA.

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