⚡️ Today’s level up ⚡️

Last week I talked about the value of harnessing your attention so you can focus on high value activities.

In this edition, I’ll share how to turn that high value focus into gaining the attention of the right stakeholders at large companies by deconstructing the exact blueprint I used to generate $50M TCV in less than 4 years.

It’s all about using a persona-based transformation approach.

Let’s go!

Read time: <7 minutes

Transformation deals in SaaS require one thing: Enabling a legacy for the right executive

If you are selling SaaS into enterprise companies, you know it takes time and multiple stakeholders’ input and approval before the deal closes.

In today’s macro economic environment, increased scrutiny and rigor is being put in place for every deal – making it even more challenging for sellers.

However, there is a special place for a hyper-strategic seller, what I call a Category of One Seller, who is closing above average sized deals, even in today’s constricting environment.

What’s their secret? They know one key thing – how to enable a legacy for the right executive.

→ If you’re a part of the Make More Hustle Less Club, be sure to watch Session 7: Build a Transformation Mindset using my discussion with Vin Varma, a former executive at a Fortune 10 company where we talked about how tapping into his legacy got a multi-year, multi-million dollar deal done at a notoriously slow-moving organization.

How do you find the right executive?

Let me rewind the clock to 2018 – 2022, when as a strategic SaaS seller for a mid-cap public conversational AI company, I led the charge as an individual contributor on winning a total of $50M in total contract value across 14 opportunities with 11 new logos.

They all followed the same blueprint, which was enabling a head of their contact center to have a larger seat at the table with their CEO.

Historically, customer care had been neglected by most organizations, taking a back seat to sales, marketing, and other corporate initiatives – leading to the default motion of outsourcing customer care to the lowest bidder in far-off countries.

You don’t have to look far for examples of how bad customer care is for most large organizations, but most executives needed an operational blueprint (not just a shiny new product to test) to be able to make considerable change, and do it in a way that left a lasting legacy.

The 3 key ingredients that helped me close (with an amazing account support team for each deal) were the following:

1. 1. A clearly identified persona
2. 2. A logical blueprint on how to transform
3. 3. A trusted network of established executives

→ Pro Tip: Look on LinkedIn or SalesNav and identify executives that have been hired in the past 24 months. It’s not a guarantee, but I have found that long-tenured executives are ok maintaining the status quo – it’s obviously working for them, so you are better served aligning with executives open to transformative change. Those who have been brought in within the past couple of years are generally open to bold, new ideas – especially ones that are logical and backed with sound data (more on that below).

Rethinking a stale sales process to become an impact maker

Most sellers, even those managing strategic accounts, would agree that these are pretty straightforward insights, but where Category of One Sellers differ from other sellers is on the execution.

Most transactional sellers:

• – Driven by activity
• – Use existing marketing material
• – Talk about product, budget, and delivery
• – Focus on competition, features, and comparison
• – Engage with anyone who will say yes to a conversation

Category of One Sellers:

• – Driven by impact
• – Develop unique insights
• – Talk about outcomes, risks, and change
• – Focus on the customer, transformation, and legacy
• – Stress test the insights with the persona and key people around them

When I started with this company in January of 2018, I joined a team of 5 new logo hunters focused on strategic accounts (a part of a broader 300+ person sales organization).

It was a classic land and expand model where we were hired to sell $250K “starter” packages across our list of 50 strategic accounts, and then hand them over to a Client Partner to expand the scope and size of the account.

However, I knew a few things to be true:

1. 1. It was going to take a long time to close a new enterprise logo – even a $250K package
2. 2. Selling a $250K packages was going to be perceived as solving a $250K problem, but I wanted to solve $250M problems
3. 3. If it was going to take 6 – 12 months to get a deal done of any kind, I needed a better strategy to focus on solving massive problems

I started by deeply analyzing one of our most marque and “mature” customers. Mature in the sense that they were spending a lot of money with us to do something different – lead their entire company behind transforming customer care.

It was a unique approach, and one that was getting terrific results for them:

• – Going from worst to first in customer satisfaction in less than 5 years
• – Transforming how their agents worked and got paid
• – Improving their total earnings per share

This was something that could be replicated, but not easily enabled with a $250K starter package.

I further dissected how the deal was won (it was engaged creatively at the highest level with our CEO reaching out to their CEO).

I then read everything I could about the deal and how they were transforming their business (they enabled any customer to reach an expert at any time).

This was juicy information, and I’m glad I did it early on during my onboarding, because it turned out to be a transformation blueprint I could help design a buying experience around.

The system for a persona-based transformation buying experience

Being armed with this insight was a breath of fresh air, because I generally liked to be creative with my selling, and this created an elevated platform on which to do it.

It was also one where, with the right system in place, I could repeat the motions with each big prospect, but it feel like a completely unique experience to each of them.

Here are the 5 components of this persona-based transformation system, something I adapted from the McKinsey framework I posted about recently.

Component 1 (Gather Facts): Understand one persona deeply

This takes going beyond identifying and connecting with the ICP (Ideal Customer Profile) most sellers are trained on when they join a company.

Instead, it’s about analyzing everything about a role that your product and services could impact the most, and then architecting a high quality buying experience that makes it very easy for them to say yes.

I say persona here intentionally because I discovered that the title of this person varied greatly at the organizations I pursued and they were typically in the VP – EVP area of the organization with access to the C-Suite (high enough to enact change, but not too high up to engage).

At the heart of it were 3 things:

1. 1. Deeply understanding what someone who is in charge of customer care has to do (ask who is that persona for your business?)
2. 2. Identify all the change enablers (levers to pull) and change blockers (hurdles to remove)
3. 3. The specific language that they use to measure success and failure

Dependent on the size of your organization, gaining this knowledge from experts is not that hard. Sources include:

• – Research
• – Your customers
• – Your executives (be conscious of any hires in your org that come from your customer base – they are the best ones to build out this blueprint with)

The key is dedicating to this upfront work, especially if you can do it at the beginning of your role or start of the year, and then it will be easier to adapt to each prospect as you gain experience.

→ When it’s done right: They will become your Mobilizer of change and do the selling for you when you’re not in the room.

Component 2 (Understand the Big Picture): Help the persona think big – a legacy worth leaving behind

Solving a big problem at once is going to be a hard sell, however you do need to zoom out to paint a big picture.

This is where things will differ from prospect to prospect, as everyone will be motivated by different factors.

However, there are pretty standard places to start, and then through quality connection with the executive over time, fully understand what’s important to them.

Note: these are not the general outcomes sellers generally talk about (ROI of using a product), it’s about one level higher – what do they want to be known for?

• – Cultural impact (how does this change the face of their industry or org?)
• – Vision impact (how does this change how things are done at their company?)
• – Economic impact (how does this change how the organization can access or preserve capital predictably?)

→ When it’s done right: This will become the headline of your narrative proposal.

Component 3 (Build an Issue Tree): Break the idea or issue down into the smallest components

After getting an executive to think big, they and their team need to act small.

The key is to break the impact down into it’s smallest parts:

1: Profits are down

1.1: Margins are thinning

1.1.1: Customer support phone volume is up

1.1.1.1: Operating expenses have increased, while customer satisfaction has decreased

→ When it’s done right: This will become the meat of your narrative proposal.

Component 4 (Make the Impact Clear): Illustrate how things can be different

This is where a lot of sellers fail, as this is when they start to pitch a product, its benefits, its features, and how it’s so much better than the competition.

That’s what leads to RFPs, being put in a box, or needing to have discussions on securing budget, and so on around the sales-buyer hamster wheel.

This is not the time to talk about product, this is the time to position a whole new way for the company to operate which will enable the executive to achieve their legacy.

This component was the key one that helped me personally earn $3.7M over that four year period, with $3.5M of it coming from the last 3 years.

It’s not about leading with your product, it’s about leading to it. You’re selling them on the blueprint of how to operate completely differently, not a new piece of technology with an ROI.

On each deal, I set the standards and painted the story, but ultimately it was enabling the account team and the subject matter experts to really position the transformation.

For leaders of customer care, we showcased how to transform their contact center operations by using a step-by-step approach.

It was less about product and features and showing them what’s wrong with voice agents today and how they could be leveraged as the most important asset for the company and go from answering phone calls all day (that are expensive and everyone hates) to managing a fleet of automations that handle customer care inquires in a way that is highly satisfying.

This transformation plan gave the agents a whole new career path, but required a complete overhaul of how they operated. That was a novel idea.

Nobody was talking about this – not even the big consulting firms. That gave us a huge advantage and momentum for them to lean into our expertise, cutting out the competition without ever needing to talk about them or compare ourselves to them.

This was the key to not asking for budget, but unlocking budget (in the range of $2M – $14M a year – with a net new logo!).

→ When it’s done right: They will want to speak with other executives to understand how to de-risk the implementation (be sure to have a trusted network of executive peers they can talk to on a regular basis).

Component 5 (Enlighten the Stakeholders): Make it clear for them to communicate this change internally

A common approach big consulting firms use is The Pyramid Principle. It was created a long time ago by Barbara Minto during her time at McKinsey.

It’s a great tool for making it easy to understand your plan (while making it hard to dispute).

It works like this:

– Start with the Answer: Bring the Most Important Idea to the top (your proposal headline). Here’s an example I used with a major global airline: “Turn every irregular operation (i.e. flight delay) into a moment of delight for customers.”

– Summarize 3 Arguments: These should be logical arguments on why change needs to occur that support the Most Important Idea. Examples for me included things like:

• • 89 million phones a year are costing $534M
• • Customer hold time is over 18 minutes and CSAT is 63
• • 85% of customer care agents are on voice and turnover is 56%

– Evidence: These are the real-life data points that support your arguments. Examples I used included things like:

• • CSAT scores improve an average of 20 points on messaging vs voice calls
• • Agent attrition is cut by 50% when they switch from voice to messaging
• • 90% of issues are resolved the first time

→ When it’s done right: Your executive will help you write the proposal and give you all the data you need to move the deal forward.

Hope this was helpful.

Next year I will be launching more products and services to enable you to become a Category of One Seller. The best way to get them first (and try them free) is to join The Make More Hustle Less Club.

See you in 2023!

Was this helpful? Now read this: The Simple Strategic Sales System I Used to Build a $27.3M a Year Book of Business in 4 Years.

When you’re ready, here are 3 ways I can help you:

1. Get the exact system I’ve used to go from earning $200K to over $1M a year in SaaS sales without burning out here. (Last chance at $77 before price goes up in 2023)

2. Join a community of Purpose-Curious™ sellers in the Make More Hustle Less Club where we develop a personal operating system together here. (300+ members)

3. Book a 1:1 strategy session map out your best year in SaaS sales here. (My hourly rate increases to $1,000 on January 1st)