When I joined Loom as the company’s first sales hire in January of 2020, friends and colleagues asked me questions like "What will you be selling?" and "What’s your quota?"
My answers were less straightforward than I might have liked.
"I’ll be focusing on selling Loom’s upmarket offering to enterprise customers, and I’ll work with my leadership team and board to establish goals and quotas based on our alpha and beta findings."
This reply mostly drew blank stares, crinkled brows, and wary nods. It’s not a common answer from a sales leader to these questions, so I wasn’t surprised at the tepid response.
However, the past several months have only bolstered my belief in the impact that a sales team can have on an early-stage product. Hiring salespeople before you have a product that’s ready to go-to-market might be a high-leverage way to test your product-market fit, pricing and packaging, and product’s readiness. Here’s why.
Salespeople Uncover Customer Pain Points
Almost every sales methodology emphasizes the importance of deep sales discovery to successful sales teams.
Whether it’s the Sandler Sales methodology’s "uncovering levels of pain" to get to the root cause of a prospect’s buying motivations, or the Challenger Sale’s "powerful requests" method to understand how serious a prospective buyer is, sales professionals use decades worth of research and experience to understand their customer’s buying motivations.
As a result, the types of customer insights your sales team can gather are fundamentally different than those you’ll receive from a customer survey or market research interview.
This isn’t to discredit surveys or market research; both deliver critical insights about your customer sentiments and journey. To best quantify a customer’s willingness to pay — and to drill down into someone’s true motivation for purchasing a new workplace tool — I’d bet on a sales professional’s ability to deliver actionable insights ten times out of ten.
What differentiates a sales-first approach is taking active steps to build a relationship and to leverage these learnings to create and sustain a successful partnership.
There’s More to Sales than Being a "People Person"
There’s a common stereotype that great salespeople can "sell anything to anyone." This idea might evoke the image of a Glengarry Glen Ross-esque, shark suit-wearing salesperson bragging about their ability to sell "ketchup popsicles to a lady wearing white gloves."
Sales reps are people first, not opportunists seeking to dupe the unsuspecting.
A salesperson who advertises that their product solves all of your problems without establishing a deep understanding of your goals and obstacles isn’t doing the sales process justice. Being a "people person" and exhibiting unerring confidence in your product will only get you so far in sales.
What this means for sales professionals: we need to take a holistic approach to evaluating the product we represent, the needs of their prospective buyer, and apply this information to the prospect outreach and sales process.
That said, there’s a bell curve in the sales profession. The best salespeople exhibit similar characteristics that separate them from their peers — and they might not be what you think they are.
Curiosity and caring are key.
The best salespeople I’ve met in my decade in the profession embed curiosity about their customers into their sales strategy. Great salespeople get to know their customer’s business, career goals, problems, and what they do on the weekends.
The answer may or may not be relevant to leverage points in the course of a deal, but they usually lead to interesting answers, and are crucial because the best salespeople build partnerships and trust. You cannot be a partner if you don’t care about the other party. You cannot care about someone without being interested in them.
I learned this fundamental truth in 2015 while working with an upmarket customer at a publicly traded company with my early-stage startup. This customer was an early adopter of our technology, and had an impressive vision for what could be accomplished when applied across his mature company’s growth team.
The three-month pilot we engaged in was set to end on Halloween. At the time, closing this deal meant a lot to me as a new hire at my company. At 6 PM on October 31, we connected on a call and this person said, "Pete — I’m all in on what we’re trying to accomplish, but I need more time to sell it to my bosses. I’m taking my kids out trick-or-treating right now. Can we talk tomorrow?"
Our agreement expired that evening, and I walked away empty-handed in the short term. Despite this temporary setback, we shared a human moment which led me to respond by saying, "Go, enjoy your kids. We can pick this up next week."
While it hurt in the short term to not land that deal, the partnership we’d developed deepened in that moment. In the next month we closed the second-largest deal in my company’s history, and eventually helped this same customer to get a promotion based on the results he’d delivered with this deal. Beyond that, we’ve stayed in close touch over the years and have even worked together at our next companies.
Successful partnerships are built with care. Working in sales shouldn’t change this.
How does hiring curious and caring salespeople help me bring my product to market?
Sales is not the only profession that’s curious or caring around their customers by a longshot. Your customer support team shows their care every day based on the number of tickets they resolve. Your marketing team takes painstaking efforts to author and distribute impactful surveys to better understand customer needs. Sales doesn’t have a monopoly on customer curiosity or care, so why invest in them early?
The answer is that working in sales grants people the ability to ask different types of questions to understand the true drivers behind customer decisions.
- "Why is that feature so important to your company?"
- "What do you stand to gain if this project is successful? What do we risk if it isn’t?"
- "If you didn’t have this feature, is there any impact my product could have on your business?"
- "It sounds like this tool is more expensive than you think it’s worth. How are you thinking about ROI and what would make this product worth that price point?"
These are all questions sales professionals are trained to ask, and can deliver back to your business from its earliest days. Understanding what features lead to tangible impacts, what objections are hurdles versus roadblocks, and understanding how your target customers perceive the value of your offering is crucial to your long-term success.
An investment in sales prior to the launch of your product provides you with valuable input around your current product-market fit, and helps you outline the gaps in selling to your target customers.
This information is just as valuable to your business six months before you launch a project as it is six months later, if not more so. Early investment in sales can help you avoid the hidden icebergs of non-impactful product investments and better understand your customer’s buying process as well.
Tailor Your Sales Investment to Your Business
Context matters for your early sales investment. If you’re a primarily outbound B2B enterprise play your strategy will differ dramatically from a product-led growth company that benefits from strong organic interest.
Does your product offer a free trial? Is there a freemium version? Is your ideal customer profile well-defined, or is there broad application for your target?
The answers to each of these questions will alter your approach to early sales investments, but you also need to consider this question across the board: "Will sales help me better understand my customer’s problems and willingness to pay for my solution?"
The answer is usually, "Yes, and earlier is better."
That said, it’s important to consider setting guidelines to make early sales an additive group to your company. Here are a few suggestions to consider:
1. Avoid feature-specific and deal-specific feedback.
Some of the criticism of early sales teams centers around the short-sightedness of, "build this feature for this client so that we can win this deal." Establishing systems to collect detailed feedback, review common customer problems, and defining the risk or reward of different roadmap investments will help to sort signals from the noise.
Tools like Productboard can capture customer feedback and establish a common language for teams to interpret and weigh customer feedback in roadmap discussions.
2. Anecdotal feedback matters.
Sales teams should look for customer stories that highlight the power of their solution or the impact of a missing feature to that business. These stories help to humanize your customers, and contextualize how your product is used in the real world. Share these anecdotes broadly with your company early and often, as I’m a firm believer that this fosters a customer-centric company — especially in the early stages.
3. Walk before running when setting early sales quotas.
It’s important to understand the psychology of salespeople before you invest in that team, and the intrinsic connection between goal-setting and prioritization. Chances are early on sales quotas will involve a decent amount of guesswork.
If you set quotas too high, you risk de-motivating your early team as a result of subpar attainment. If you set quotas too low, you risk paying salespeople out in an untenable way that puts your business at risk.
For your initial sales hires, consider offering a greater-than-standard equity package and an attainable-yet-upside limited MBO-based quota. This way you can be sure to incentivize business-positive behaviors while learning critical information about your early customers.
4. Integrate sales at every level of the company.
Sales teams that are siloed from cross-functional communication with marketing, product, engineering, design, and other teams are set up to fail. For sales teams to be successful they must be considered a conduit to other teams, and be empowered to freely and regularly surface their customer’s feedback across the company.
Similarly, sales shouldn’t be a solo act at a company; this will lead to short-term planning and stunted innovation. Be intentional about integrating early sales teams into your company and building cross-functional empathy; this will set the foundation for long-term success.
Notes from the Field
Six months after joining Loom, I’m thankful for the opportunity to build a sales team from such an early stage. Early learnings from customer conversations helped me to prioritize feature requests based on impact or risk to that organization, helped us focus our work in determining ideal customer profiles, and helped us surface different elements of our customer’s voice as we bring our upmarket offering to general availability.
I think back to those early conversations where I was asked, "You’re joining a company six months before they release the product you’ll be selling?"
Now I think I’d reply more confidently with, "Yes, that’s when investing in sales made the most impact on our business and its customers." Because it did, and it might for you, too.