Sales Masterclass #2: The 4 Pillars of Successful Startup Sales

Learn about pain, product, clarity, and trust; building your minimal viable sales stack; and the SPIN methodology. Featuring Avi Wiesenberg

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Episode Highlights

Sales get  a bad rap with founders. It's easy to picture it as the territory of slick, smooth-talking types, using the over-the-top tactics a-la The Wolf of Wall Street. But this is a dated view: Sales today isn't about schmoozing over drinks, but about expertise and understanding. 

Software sales mean  knowing your product inside out, understanding the tech landscape, and being savvy about your potential clients' needs and structures. Founders often act as the sales team by default – because you know your product best and nobody else can sell it as well as you can.

In this masterclass, we're going to break down the sales process into four pillars, walk through a real-life example of a sales method that works, and wrap up with a look at the essential sales stack. 

What you’ll learn:

• The four pillars of sales: pain, product, clarity, and trust

• The SPIN methodology

• The basic sales stack

Meet the expert:Avi Wiesenberg is a strategic advisor, early-stage investor and sales leader with over 15 years experience, with a focus on scaling hyper-growth SaaS startups. He has previously held revenue leadership positions in Oracle, ClickTale, and SimilarWeb.

The four pillars of your B2B sales process:

1. Pain

The primary question of sales is why someone would buy your product. Nobody jumps out of bed excited to purchase enterprise software. There’s only one reason that would lead them to do so:  pain. The kind of pain that blocks them from reaching their goals – whether it's getting a promotion, being seen as an innovator, or getting a shout-out from the CEO.

Whenever you think about pain, you have to remember two things:

• Everybody hurts… differently: every stakeholder in a deal has unique worries and ambitions. Your strategy needs to be inclusive enough to address each person's concerns in the decision-making chain. In big organizations, this might mean understanding and addressing the diverse pains and perspectives of dozens of stakeholders.

• Inertia is your biggest competitor: for many founders, particularly those who have a disruptive or innovative product, it might seem like they are operating in a clear field with no competition. They are wrong: their biggest competitor is the status quo. It’s on you to show that your solution offers more value than the familia, seductive allure of doing nothing and sticking to what the organization already does.

2. Product

In most cases, founders are not identical to their customers, which can distort their worldview and the importance they place on their own product. . A founder gets a lightbulb moment to solve a problem, validates it, pitches it to investors, and boom – a company is born. But the problem you've been obsessing over for the last year or two? It's not necessarily what your customers are obsessed with.

Getting past the ‘why should I care’ threshold. Customers only care about what’s happening in their company. When you're selling, you've got to pivot from the problem you started with to the pain points your customers are voicing.

A simple way to do this is to  start with the problem you identified, then ask your prospects how they handle it. Probe into their current situation and look for other related issues where your solution might fit.

Is your product a must-have or nice-to-have?  Getting the sale across the line  will  be difficult if it's perceived as non-essential. You need to reframe the product's value proposition to make it indispensable.

Cool is not enough. Your product’s  'coolness factor', especially in SaaS, needs to be tied back to its practical value. A visually appealing product is great, but it must clearly address and resolve customer pain points to be compelling.

3. Clarity

Keeping your prospects engaged and committed is a key part of the sales process, and it’s your job to eliminate any reasons for them to step back from the deal. 

Keep your messaging consistent.  Your sales pitch and deck need to tell the same story as your website or your ad . For instance, if your website markets you as the ideal solution for SMBs, telling a client that you're the top choice for large enterprises wouldn't make sense.

In early stages, you have more flexibility. There's likely less information about your company online, allowing you to create a perception that might be slightly ahead of your current reality. For example, you might be able to get away with less transparency on pricing. But tread carefully: While a little creative framing can be helpful, transparency and honesty are the foundations for long-term success and credibility.

4. Trust

We buy from people we trust. Trust is built by being transparent, showing genuine curiosity, and offering a product that truly impacts your prospects’  lives. 

To establish trust, you need to see your role as more than merely  presenting a product; you’re expected to guide your prospects through the sales journey, leading them confidently towards a purchase they feel confident in making. To do so, you need to understand the dynamics of your stakeholders within their organization.

In the past, face-to-face meetings provided cues about a stakeholder’s level of involvement and decision-making power. In the era of video calls, these cues have changed, but they haven't disappeared. Pay attention to the dynamics of the call. Assess the confidence level of each participant within their company. Do they bring in other key people effortlessly? Do they follow through on what they promise? How swiftly do they act on decisions? 

But don't rely solely on observation. Ask direct questions: Have they purchased similar products before? Who else should be involved in this decision? How are purchases typically made in their organization? Do they have the budget for the product? 

These inquiries are expected and legitimate. But remember that this should be a natural conversation, driven by your curiosity and desire to understand how you can best help them - not an interrogation or a box-ticking exercise.

Addendum 1: SPIN Sales

One basic sales methodology that captures all that beautifully is "SPIN Selling by Neil Rackham. The approach has four parts: 

• Situation: Understand the prospect's current status quo to reveal a pain point. For example, asking, "How are you managing this process currently?" can lead to uncovering problems with their existing methods.

• Problem: Dig deeper into the issues they're facing. "What challenges are you encountering with your current approach?" helps identify specific pain points.

• Impact: Explore the potential impact of these problems. "If this issue was resolved, what would be the value?" 

• Need-Payoff: Let the client articulate the personal or business benefits they'd gain from your solution. Asking, "If our product could give you two extra hours a day, what would that mean for you?" helps clients visualize the tangible benefits, making the value proposition more personal and compelling.

Using this approach, you guide clients to realize how resolving their issues can lead to significant improvements in their professional or personal lives. It's about helping them see the 'lightbulb moment' – how your solution can positively impact their world. If you want to dive deeper, we recommend looking into it!

Addendum 2: Building Your Sales Stack 

There are many, many sales tools that you can potentially buy…

But if you’re starting out you should probably go with something much leaner:

• Customer research: The first step is understanding your clients. Use LinkedIn and other public sources to gather as much information as possible about your prospects. 

• Call recording: make sure to use the recording feature of your video call platform. The recording would allow you to review details you might have missed. It also acts as an organizational memory bank, providing insights for future interactions.

• CRM: This is where you keep your list of prospects dynamic and updated to maximize sales opportunities (see Keren's Mir's masterclass for a deeper dive into effectively using CRM).

• Engagement tools: Tools like HubSpot or similar platforms help you manage your outbound efforts. Documenting and tracking these activities alongside your other sales efforts helps maintain a cohesive sales strategy.

Embracing Your Role as Salesperson #1

By now, we hope it’s clear that mastering sales isn’t about showmanship, but revolves around understanding your product, market, and customer needs and making impactful connections with your prospects. Keep these principles in mind, and stay curious and genuine. And sell.