Sales is now, more than ever, the lifeblood of your company— providing the necessary oxygen to keep you alive and thriving. At my first startup, ReTargeter, we generated well over $10MM in revenue over a couple years with ~30 people of which only 4 or 5 were Account Executives (AEs) with some SDRs — that’s equivalent to ~2MM sales quota per AE. Back then, we were building a startup just after the 2008 market crash— capital was scarce and people working in startups knew what they were getting into.

In this post, I codify my learnings from building ReTargeter during a recession so you can accelerate your sales motion even though you are already likely firing on all cylinders with extremely constrained resources (time, talent, money):

Prioritize where you focus your efforts— what fires to let burn, what fires to put out, and how to play offense even if you’re forced to be on your back foot.
Leverage your relationships (social capital) to access a broader network to lubricate your sales motion.
Systematize your sales motion with simple, cost-effective processes and technologies.

Read Me: The Working Premise

This post was written for Early-stage B2B startups who have a valuable product that more customers ought to be using. Even if you have a valuable product that you know should exist in the market— it won’t survive in this economic environment unless you can grow your sales efficiently because:

You will eventually run-out of operating capital unless you already have a path to profitability that doesn’t require cutting operating expenses so deeply that you end up delaying inevitable death.
You will destroy the chances to secure additional investment from institutional VCs. Across the board, institutional VC investors have created growth-efficiency mandates that prevent investment opportunities from being put to partnership unless they demonstrate strong margins and a solid burn multiple.

To get the most out of this post, we assume you have a product people are paying for and are continuing to happily pay for:

You Have Identified Your Target Customer: The types of customers (SMB, Mid-Market, Enterprise) that are the best fit for your product. This will help you focus your efforts on the right customers and increase your chances of success. You may be serving more than one type of B2B customer—that’s ok— however we assume you can quickly assess which customers are more valuable for you to secure.
You Can Articulate Your Target Customer(s) Core Attributes: you understand their business including: their definition of success, key goals, pains and challenges. It may take some time and experimentation to fully understand your target customer(s), but it's worth the effort to ensure that your product or service meets their needs and is successful in the market.
You Can Articulate Your Compelling Value Proposition: you can simply and easily communicate how your product will help your customer solve key challenges, ease their core pains, and realize their most important gains.

1: Lead the Motion

We are favorable to founder-led sales for numerous reasons (we’ll cover the prioritization challenge in the section following):

Passion and Vision Sells: Founders are often the ones with the most passion and vision for their product or service. Speak to any effective salesperson and they will tell you that belief in the product is a huge determining factor of a successful sale.
Trust and Credibility Speeds Things Up: Founders often build trust and credibility with potential customers more easily than salespeople. This is because other salespeople are not directly involved in the creation of the product, or are not experienced in the relevant industry/market. This is especially helpful when speed matters— direct outreach to prospects (we will cover more of this later in the post) leads to higher conversions and faster response times. The faster contracts go live, the faster cash hits your bank on a recurring-basis.
Minimizes Cash Burn: Every action has to contribute to some sort of ROI. Founder-led sales are a more cost-effective way to bring in new business without the need to hire (or expand) a full sales team, yet.
Retain Customers and Improve Product: Founders who are active in sales can receive immediate feedback from customers and translate the important feedback into their product.

Don’t worry about scaling yourself out of the sales motion for now since you don’t have a chance at scaling unless you get the sales foundation in place first. Better to sell to the point where you earn the right to hire and train additional staff.

2: Prioritize Especially When You Feel You Can’t

Your time and capacity to sell will always be constrained by the following:

The need to retain customers which includes a combination of customer-success, learning, and engineering/product input— keeping your customer happy is important as there is no point selling unless it leads to recurring revenue.
Engineering/product efforts to continue to improve and stabilize the product— you will discover your product’s limitations, bugs, and constraints as more customers use it.

Do your best to try to balance both— it is a combination of offense and defense. You will have to endure for as long as you can until you can afford to hire more help. This phase of early-stage startups requires incredible grit and endurance— the workload is insane and no one without a clear mission/motivation would sign up for it. To make it through the gauntlet of this phase, do one or more of the following:

Rigorously prioritize your efforts by weighing the ROI of each action/priority and choosing your best bets. When the ROI isn’t clear, I suggest using Brian Balfour’s growth experiment system by ranking the following in terms of — low, medium, high:

Size of upside if experiment is successful (Low, Med, High).
Probability of success (Low, Med, High).
Resource demand (Low, Med, High).

Prioritize the initiatives that have the highest gains if successful, high probability of success, and low resource-demands. Deprioritize the low probability and high-resource demand initiatives.

Say ‘no’ to a lot more than you feel comfortable with. The reality is you are going to have to be more ruthless (black and white, even) about your time— especially when your instinct is to be helpful to everyone. Early-stage founders are typically over optimistic with what they can achieve and have a cognitive bias to saying ‘yes’ — this is a strength and a weakness. Here are a few example of automatic ‘no’ responses you can start practicing:

When the ask isn’t clear and cohesive — say no and tell the individual to clarify their ask:

1) What outcome you want to achieve, and
2) What input specifically they need from you and why. The individual will more than often not gain clarity and realize they didn’t need your input to start with— they were just defaulting to using you as a soundboard/resource versus thinking structurally.

When the request is clearly something someone else can help with— copy that someone else on the communication thread and ask them to take care of it. Most employees at early-stage startups should know what they signed up for— startups are on alert around the clock and must respond with great agility.

Find creative ways to leverage your time either by delegating, outsourcing, partnering, or exploring technology solutions. Few examples:

Give equity to key advisors who can open doors to many enterprise customers— we have seen this accelerate GTM motions to go from $0 to more than $7MM in revenue within a year.
Partnerships with key players in your ecosystem. While partnerships can be slow to form, their pay-off can be large— imagine if one relationship could open doors to 1000’s of customers at once?
Open AI’s ChatGPT can help synthesize meeting minutes, give you the TLDR on long email threads, and even write draft emails on your behalf.

3: Leverage Your Social Capital

Social capital is resilient to economic downturns. When you are constrained on resources to invest in paid acquisition (sales, marketing, and PR, for example) — activate your existing network and ask for introductions to:

Potential customers.
Influential nodes.
Key decision-makers.

We recommend using our Request for Introduction (RFI) playbook to get this done— you can use our first-principles playbook for business development, sales, fundraising, and hiring, for example.

Social capital is built by a combination of give and take— being helpful upfront and demonstrating value, and making requests so the other party can reciprocate— it is a virtuous cycle that builds over time. Few ways you can build trust in relationships:

Demonstrate Competence: When it comes to enterprise-grade customers, you will have to offer a proof of concept to demonstrate the value of your product while appeasing their fears.
Communicate Frequently: Open and honest communication is essential to building trust. Listen actively to what others have to say and address their concerns and questions promptly and honestly.
Honor Your Word: Being consistent in your actions, words, and behavior builds trust over time. When you consistently meet your commitments and expectations, others begin to rely on you and see you as trustworthy.

Getting an introduction is only the first step. Just because someone opens the door to a potential customer, it doesn’t mean you can immediately go into ‘pitch-mode’ with your product. Many enterprise-grade customers require you to navigate a larger, more complex process— this process isn’t always coherent or clear to individuals in the organization either.

Therefore, you will have to play the role as trusted advisor to map the enterprise you are selling to. Here is a simple questioning framework you can use— use it as a guide for your information gathering. This framework helps establish trust, build rapport, and ultimately increase the likelihood of a successful sale:

Goals (G): Understand the organization's objectives and priorities.

What are your organization's short-term and long-term goals?
How do your current initiatives align with these goals?
What are your key performance indicators (KPIs) for success?

Structure (S): Determine the organization's structure and key stakeholders.

Can you describe your organization's structure?
Who are the key stakeholders involved in the decision-making process?
Which specific departments or teams would benefit most from our solution?

Decision-Making (D): Learn about the decision-making process and criteria.

How does your organization typically make purchasing decisions?
What are the most important factors you consider when evaluating a solution?
How long does the decision-making process typically take?

Needs (N): Identify the organization's pain points and requirements.

What are your current pain points or challenges in achieving your goals?
How have you gone about addressing these challenges to date— what’s worked well and what hasn’t?
Assuming our solution does exactly what you want, what value do you envision it will bring?

Budget (B): Assess the organization's budget and willingness to invest.

What is your budget for this type of solution?
How do you prioritize budget allocation for different projects?
Are there any financial constraints we should be aware of?

Challenges (C): Discover potential obstacles and how to overcome them.

Are there any internal or external challenges that could impact the implementation of our solution?
How have you dealt with similar challenges in the past?
What resources or support do you need to overcome these challenges?

4: Lay the Tracks As You Go

As a founder leading the sales motion solo in your early-stage startup, there are several simple processes, systems, and practices you can implement to lay the rails for your future sales org. If you are leading the sales motion to start, it is hard to document everything you are doing without the assistance of a simple process and some technology— it’s like trying to edit yourself while you are writing.

However, assuming your sales motion gains momentum, you will hit a point where you can invest in sales support. At that point, you want someone to be able to quickly grasp your sales motion so you can start to take a step back. Here are a few things we suggest:

Document Your Process: you can either record Zoom calls, use an AI assistant like Gong.io, record and transcribe meetings with Otter.ai, or even record a pitch using Loom. Furthermore, all successful sales correspondence can be copied and saved to a folder so someone in the future can review and reproduce your success. You don’t need to edit the material heavily— it just needs to be there so at some point you can (with the help of future sales hires):

Create best practices, scripts and templates.
Develop FAQs and objections-handling training.
Create templates for proposals and contracts.

Use a Very Simple CRM: if you have the luxury of using Salesforce or Hubspot— great! In absence of that, you simply need to use something much faster, cheaper, and customizable like Notion or AirTable— these are simple databases that you can use to visualize data on your sales process. To start, you only really need to track: 1) Where in the pipeline your customers are (first meeting, demo, contract, for example), and 2) track key decision-making information (e.g. internal champions, buying process), and 3) Dollar value of the pipeline (leads, in-contract, and probability of close).

5: Package & Price

Most early-stage founders leave money on the table when it comes to packaging and pricing.

First, founders often underprice their good product for their ideal customer. We have seen a founder succeed by running experiments by adding 0’s to their price— imagine how quickly your business improves if most of your customer base pays you more by a couple of decimal places.

The simplest way to get over the hump is to price on value. For example, if your customer uses your product for 3 months, 6 months, 12 months and beyond— what is their ROI? It is likely orders of magnitude more than what they pay for your product. Most founders can calculate a customer LTV for themselves — but you must also calculate what your LTV is to your customers. This is best done with a simple value calculator in Google Sheets where you identify those key value drivers—on both the revenue and cost side.

The corollary to this is founders usually overdeliver value without packaging their product(s) in a way that maximizes revenue generation. For example:

Is there an opportunity to modularize your product similar to Zoom and Intuit? If you can charge in modules it helps you land with one and expand from there. This could 2X your revenue per account while lubricating your sales motion as it is often easier to sell more to happy customers than to new customers.
Is there an opportunity for you to earn more money from your target customers by delivering the same value but charging them in different ways? The 3 Part Tarif (3PT) model works well for this— you can earn SaaS Fee + additional fees based on usage above a certain amount.

In Summary

As you gain more experience selling to enterprise-grade customers, continuously iterate and refine your approach. Incorporate feedback from your customers to improve your product and sales process. By following these practical steps, a small startup can sell their product to enterprise-grade customers at speed and increase their chances of reaching net-zero and beyond.