A startup’s guide to building a winning sales strategy

Having an established sales strategy can sound like a good thing. But if you’re a founder, it might not be.

Early-stage sales strategies that attempt to lock in ways of working too soon can lead to disappointing outcomes. That’s because startups often need to discover what works before setting details in stone. What works a few times at first won't necessarily always close deals in the future.

Savvy founders approach the creation of a sales strategy through conversation, trial and error, and, yes, some uncomfortable feedback from prospects. Here’s what you need to know about the process.

Challenges of early-stage founder-led sales

Early-stage sales strategies can fail for a variety of reasons—from designing them for a misjudged target audience to not having enough data to understand if they're truly succeeding. The following are a few common issues every founder should prepare for.

Conversations aren’t consistent

Some prospects immediately see the value in a product or service, while others may have a difficult time understanding it. So, while in one conversation you may feel that your offering is on the right track, in another you may start to doubt it. Remember that it takes time to compile enough feedback and sales data to accurately estimate your target audience’s needs, and some early confusion about them isn’t just normal—it’s an essential part of the growth process.

Messaging changes week to week

When you aren’t yet sure what messaging will resonate with your audience, you can’t draft consistent marketing emails or pitches for sales calls. You’re still navigating the startup sales process on a case-by-case basis, feeling out what narratives each type of prospect relates to.

Wins feel encouraging but hard to explain

All wins count, but early ones may seem more significant than they really are. You don’t get historically positive sales data out of just a few wins—even if they are a strong sign that your product and budding sales strategy are resonating. Don’t be surprised if what works for the first few sales doesn’t consistently work after the fact. And avoid locking down a sales motion that reflects what worked in those initial sales, as it may later prove ineffective.

Why startups should begin with founder-led sales

Smart founders treat early sales as lessons—ones that will be especially important to transmit to others down the road when the startup begins hiring and training a sales team. Here’s more on the insights that founders gain from being hands-on in first sales and the early creation of a sales strategy.

Accelerates learning about ICP and pricing

As founders navigate conversations with prospects about the startup's offering, they learn from their audience’s pushback and questions. Founders can also gauge if pricing is in the correct range based on prospects' reactions to it, and they can determine what type of audience is ready and willing to purchase the product at the current price point.

Surfaces objections no research will uncover

When founders get “in the room” with end users, they gain nuanced insights that market research simply can’t provide. Market research provides generalities, while real people can expand on the reasons why they would or wouldn’t acquire a product or service and provide feedback on the "why" or "why not" that can drive improvements to pricing and features.

Forces clarity around value, not features

End users think about benefits—how a product or service will change their work or lives for the better. And talking with prospects helps founders better understand how to describe how their offering solves users' pain points instead of listing off features. As founders develop this narrative, they're drafting an essential part of their sales strategy: the type of messaging that can drive repeatable sales content later on.

Turning early conversations into strategic signals

Instead of focusing on the steps that led to a single win (or loss), founders should monitor for patterns in their conversations with end users. They should track:

• Repeated objections: Listen for the objections that users routinely surface, like saying that the tool is too expensive or doesn’t have essential features they would need in order to make a purchase.
• Consistent drop-off points: Pinpoint when prospects lose interest. Do they turn away after a product trial? After reviewing a price quote? Knowing when people decide not to buy can help founders understand the drivers behind these decisions, like out-of-range pricing or lacking features.
• What moves deals along: Don’t overfocus on what makes deals fall through or stall; look at what pushes them along, too—whether that’s offering special pricing or providing prospects with one-on-one support to better understand the benefits of the product's features.

Choosing a sales motion that fits your business

Once your sales motion starts stabilizing (that is, it begins to routinely follow a repeatable, winning process), you’re landing on a strategy that works and that you can take into the future. But getting to this point takes some experimentation, and founders frequently try the following:

• Founder-led outbound: Founder-led outbound is a cold-selling motion in which founders directly reach out to prospects. They gain first-hand experience talking to end users and learn what messaging resonates as well as what objections people surface.
• Inbound driven by content or referrals: Founders can also drive inbound interest through content (web, social media, etc.). This marketing pulls in consumer-motivated contact, and these end users tend to be more open to the company’s offering, since they’re taking the initiative to seek more information. The conversations founders have with these prospects can reinforce what the startup is doing right, both in its product and burgeoning sales strategy.
• Product-led or usage-based sales: Product-led sales (PLS) or usage-based sales rely directly on consumer interaction with the company’s offering (i.e., through a tutorial or a trial period). In order to get the most out of this strategy, founders or early sales teams should follow up with prospects who have interacted with the tool and find out what led them to choose to purchase or not.
• In-person events: Certain products are best marketed through in-person events, at which end users get to see, touch, and experience an item. For example, a beauty product or household solution may resonate with buyers more deeply if they can see how it works live at a trade show or pop-up. Similar logic applies to consumables, like food and beverage products.

How to adapt sales as your company grows

So, your sales motion has stabilized, meaning you’ve landed on a strategy that works. Now, founders need to transmit those steps to others, which starts with creating clear documentation to standardize sales processes. This means:

• Messaging must become explicit: Founders must establish core messaging, dos and don'ts, and advice for handling consumer objections and questions as a central part of their sales strategy.
• Consistency starts to matter more than creativity: While founders can get creative on early sales, relying on a trial-and-error approach, this sales process can generate chaos among sales teams, who need reliable, repeatable steps and messaging guidelines to follow.
• The sales team should move on from intuitive selling: A founder’s intuitions can be strong, but if a sales team comprising multiple people all try to follow their intuitions when selling, they run the risk of introducing vastly different ways of working. Dispersed sales methods don’t support the consistency that companies need to regularly offer their audiences reliable messaging or service. These methods are also tricky to track, as insights on what works and doesn’t correlate to varied processes.

How Clarify brings clarity to startup sales strategies

Early-stage startup sales strategies often break down because context and processes live in the founder's memory, and these leaders can't teach sales reps these hidden tactics. They need clear documentation to demonstrate how to manage the company's messaging and sales motion, and ultimately, close deals.

Additionally, documentation will support the integration of tools like a CRM into the sales process, backing an organized approach to pipeline structuring and sales automations.

Clarify gives founders a single source of truth they can rely on when solidifying their startup's sales strategy by automatically tracking sales context, visualizing deal patterns, and reducing reliance on information that lives only in a founder's memory and notes.

FAQs

What’s the most common mistake founders make when running sales?

One of the top mistakes founders make is spending to hire a sales team before understanding the target audience and the product’s success in the market. Setting a sales strategy before defining clear workflows is also a major error.

How do you choose between outbound, inbound, or product-led sales?

There’s no one right answer, and founders can test a range of options to learn what works best. Through testing, founders gain the insights to make informed decisions on how best to move forward.

How do startups turn early sales conversations into a repeatable strategy?

Founders can identify patterns and translate what works into workflows—documented clearly enough to be taught to another person, like a new sales rep.