Congrats! You’ve worked super hard and just landed your dream job (to date, at least) as the new Head of Sales at an early-stage B2B software company.

The task is simple — or so it seems — develop and execute on a strategy that will deliver the company’s first $1mm in annualized recurring revenue (ARR).
How will you do it? We’re here to help with the playbook below.

Positioning

Market and Competitive Analysis

It’s imperative to start from a place of understanding; the industry you operate within, current trends, competitive landscape. Ultimately, the goal is to understand the terrain as best as possible. In most cases, it’s important to start narrow and go deep — super deep. While the goal might be to one day be a mass market solution, tackling a niche is more often than not the best place to start.

Unique Value Proposition

Start by conducting an in-depth analysis of the software’s features, benefits, and competitive advantages to define a clear and compelling Unique Value Proposition (UVP). This UVP will communicate the specific problems that we solve, the value this brings to customers, and why what we do and how we do it is superior to existing/alternative options.

Messaging

Building on the UVP, we’ll develop messaging/value statements that communicate the UVP to the target audience. It should be clear, concise, specific, and persuasive as to resonate with that audience in a compelling way. It should put on display that you understand their reality, what’s painful about that reality, why it matters, and how you and your software provide a solution to make it better.

Brand Identity

If you’ve done a good job of understanding your market, crafting the above messaging and by extension, your brand’s identity to match the values of your target audience is important. This way, you’ll be able to drive a natural appeal and “likeness” to the customers that you seek to serve.

Target Market

More Depth

You’ve likely done a decent job at understanding the broader market that your solution will target. But how well do you know Buyer Personas? Have you begun to compile a list that specifies how many companies fit this criteria and what the Total Addressable Market (TAM) is? In doing so, you’ll start to segment the ways in which you’ll tier the prospective customer base, considering their size, business maturity, and more. The goal here is to understand who has the highest potential for adoption and segment accordingly.

Buyer Personas

Related to the above, detailed buyer personas will allow you to bucket the characteristics, pain points, motivations, and decision-making processes of your potential customers. When you know these things, it’s important to know that how you’ll communicate and ultimately win these different types of personas can — and likely will — be different.

Segment Marketing and Sales

With a clear understanding of your target market and the personas within those, create a tailored marketing and sales strategy to tackle each. Place your bets accordingly, with your highest potential customer segments receiving the most personalized, tailored experience and then more of what we call “at-scale” outreach to the lower potential segment.

DIY and Building for Scale

Fight the Urge to Hire

This is likely to be an unpopular opinion, but our recommendation is to fight the urge to hire early on. Work alongside the founders and put your individual contributor hat on to win the first few customers. Here, you’ll refine some of the hypotheses that were developed from your research, positioning, and target market efforts above.

Tech Stack and Documentation

As you do so, start to compile the right pieces that will enable a team to scale. This includes sales automation, CRM, and most importantly - documentation that outlines the entire sales process and strategy end-to-end. You’ll be able to iterate on this over time, but it’s fundamental in being able to reference so that when you are ready to hire, you are setting the people and your team up for success.

Developing a Foundation of Data

As you do so, be sure to leverage data at each and every turn. Building the foundation for the type of information you can access and how you use it will be imperative to your achievement of that first $1mm in ARR and the culture you’re bound to develop as you start to hire. Pro tip: Present the business case for your first hire to be Revenue Operations-focused rather than a salesperson. Again, this is about building a foundation that’s designed to scale.

Customer Success

Start with Onboarding

The best kind of recurring revenue is revenue that actually is recurring. This means that you have to retain the customer after their first term. Thing is, too many companies look to far ahead to that renewal date and forget that arguably the most important part of a customer’s journey with you is when they transition from prospect to customer. Creating a seamless onboarding experience is crucial, as it sets the tone for what their ongoing relationship with your organization is going to look like.

Customer-Centricity as a Feedback Loop

Once launched, it’s not just about consistently highlighting all the good/great things that you’re delivering on. Understand what could be better, sizing up the distance between what you offer now and what the customer wants you to offer to them in the future to make your relationship even stickier. But don’t stop there. Use these insights as your compass and inform the tech/product team to drive the right kind of innovation — innovation that matters to your customers.

Success Stories

The success stories you do get, however, are your most effective way to scale. We like to call this “weaponizing your success”, where you take sound bytes from your happiest customers to lead with and attract additional, “like” customers. It’s an often underutilized way to create a sort of FOMO at scale in order to drive increased attention and interest to the problem you’re solving within a specific market and use case.

There you have it — a roadmap to achieving your company’s first $1mm in ARR. The best piece of advice that you should understand along the way is that the path is sure to be littered with unforeseen challenges, twists and turns, and surprises.

Embrace them. Understand which are within your control and which aren’t. Slot them into categories that can be used as a competitive advantage — or not. Enjoy the process and tackle the challenge with laser-focus and a smile. Pressure is a privilege.

Playbook for First-Time Head of Sales