The Stories You Must Tell To Sell

Spero Ventures
Spero Ventures
Published in
11 min readOct 24, 2018


Whitney Sales is a sales pro whose last name is literally…well, Sales. While it might seem like a goofy coincidence, it’s not an irony that she lets go unused. It’s actually an easy ice-breaking joke that loosens up most rooms she’s in. From that starting point, she’s been able to develop strong customer relationships, command the attention of prospects in meetings and yes, close sales. Big ones. In fact, Sales has helped four companies enter the Inc. 5000 Fastest Growing Companies List, from LoopNet to Meltwater to SpringAhead. At the photography equipment retailer Joby, Sales scaled the company from a few hundred thousand in revenue to $9 million a year. She’s now a general partner at Acceleprise ventures and mentors startups for Stanford University’s StartX and Alchemist Accelerator.

That experience and her abilities, which are a part of the skillset that she calls The Sales Method, is important for any startup looking to amp up revenue, whether that means closing your first deal or “10xing” your revenue. In this presentation for Spero Ventures, Sales dives into her top tips for successful sales meetings, the stories, questions and answers you need to arm yourself with before reaching out and her targeted advice for every step of the sales funnel.

The Best Style Tips For Sales Meetings

First of all, every salesperson needs to be armed with the right style. This differs from person to person, so don’t feel like you have to copy how someone else does it, but these are the key principles and tactical tips Sales recommends for sales interactions:

Connect. “Ground rule number one is to get sales prospects to accept you as a human being, as opposed to someone trying to push a product on them,” Sales says. She starts most presentations with a joke about her last name. “It’s a good way to actually connect with the audience and for you guys to understand a little bit about me.”

Conduct surveillance. “Take notes on who is asking questions and the roles of each person in the room, because it’s going to show you how people make decisions across the organization. If you have a CEO who’s driving most of the conversation, it may be a top-down organization. If you have someone who’s not talking during the conversation, what you can do is actually engage that person and bring it up based on their roles and responsibilities to re-engage them,” she says.

Mirror the customer’s tone. “Are they casual? Are they formal? Are they being friendly? Are they joke-y? Some people are going to be really serious and you need to mirror their like stiff posture and their interactions, because you need to show that you can actually interact with them. That mirroring will actually get them to follow you if you want them to break their guard,” Sales says.

Save time. Build trust. Sell more. Suss out if the client is actually a good customer for your startup. “If they’re not going to be a great customer for me, I don’t want to waste their time and I definitely don’t want to waste my time. It also will build trust. Say, ‘You know what, I know your business model. It’s not a great fit. Let’s actually stop. I’m going to put a note in my CRM to come back to you guys when we actually have what you want.’ That builds a lot of trust that when you do come back, you do actually have that feature and they’re going to be much more likely to engage with you,” Sales says.

“Your customers will actually tell you anything you need to know in order to sell to them. You just have to ask the right questions.”

Your Bank In Your Back Pocket

While it’s great to nail the presentation and relationship-building, you’ve also got to come prepared with a bank of powerful questions to ask the customer and answers to provide to the questions they’re likely to ask you. Here’s what you need in your back pocket:

  • Value-based questions. This is a bank of questions you prepare ahead of time to ask your customers. They help you understand the customer’s needs, and peel away the layers until you’ve gotten to the value they need most for their problem. Once you have that, you can figure out how best to provide that value (or if you even can provide the value they’re searching for). These questions “help me understand the value that I’m actually providing the customer,” Sales says.
  • Sales questions. “Sales questions are specifically focused on the emotional pain that this is causing for that person and the organization as a whole,” Sales says. “This is a problem. This has cost you five weeks. Can you talk me through what that process looks like? How’s involved? Oh, wow. This costs you five weeks, but then it costs your team another four weeks. Oh and then there’s a business board meeting to review everything. What happens if the information is incorrect? Wow. How does that fall back on you? That really starts to flesh out the pain points that actually relate to the day to day of that person. It makes the problem you solve much more relatable and much more valuable for them as people, so they get more motivated to solve for it. You’ve created more urgency around it, because they see it.”
  • Sales responses. “Your responses in your selling should be around, ‘Yep. I can understand how that could be a really big issue for your organization. Talk to me a little bit about how this plays out across the org,’” Sales says.
  • Value-based responses.Value-based responses are not pitches. Their purpose is not to sell. Instead, you’re educating. “You can use statistical data around how this problem developed. It could be about trends that are happening that are causing this to become a bigger problem. Or the size of the problem itself that people may not realize.Or new technology that’s developed that’s actually made this available today. All these things will actually play into establishing your credibility as a thought leader within this space and making it more likely that the customer will buy from you and trust what it is you have to say.
  • Protip: ”I like casual competitor name-dropping in my value-based responses. If I’m talking about a particular problem that a customer has, I’ll talk about how another company may have had that same problem. We actually talk to them, but here’s what I understood about the market and what was going on with the market,” Sales says.
  • Use cases. Tie use cases back to your qualifying questions. “If your qualification was about the type of tech stack they were using and how they were using it, when you talk about your use case, you should talk about the customer that is using the same technology and had a similar problem. It’s all tying back through the entire conversation in a thread and showing that you’re listening and validating the problem that they have,” Sales says.
  • ROI story. “Every use case should tie back to a ROI story. It should tie back to money or time in some way for that particular customer. It should be the pain point that you’re talking about solving for that customer. That is the benefit that you’re solving for. The end result is the ROI,” Sales says.“When you talk about your ROI, you want to be clear. You want to be concise. You don’t want there to be a lot of fluff around it. You want to see if it lands. “
  • Name the numbers. The structure of this can mirror that of a customer story. “Say, ‘It’s going to cost you this. If we integrate with you guys, this is what I would expect the result to be. I expect to be able to save you XYZ time.”
  • Spell out the results. Answer the question, ‘How will using your product impact their business overall?’ “The pain point could be that it’s costing them time. It could be that it’s costing them money. Money is usually less valuable than time for most people, especially development resources.”
  • Understand trickle-down effects. Through your sales and qualifying questions, you should have figured out how your product is actually going to impact their business from a day to day perspective. “The trickle-down effect across an organization is really, really important when you’re talking about the ROI. Tie the benefit back to the ROI story.”
  • Fall back on product research insights. “If you don’t have customers yet, most of you have done customer discovery to flesh out this problem. You should know those problems. You’ve done your product research to develop a product. You can use your customer stories that you did in your product development as your case studies. Most of them are probably friends. You can say they’re not a customer, so you can be honest about it, but you can tie it back via your customer discovery. There’s lots of ways around not necessarily having customers yet,” Sales says.

Practice asking powerful sales questions. Learn how you can make the person in front of you look good to the rest of their organization.

Scripts and Tips For Every Step Of The Sales Process

Here’s how Sales breaks down the sales process:

Qualification. Here you’re figuring out what this customer needs and determining whether or not your product is a fit for them. Usually this starts with a qualification meeting. Sales uses this structure for those:

  1. Start with the laugh. “Spend your initial conversation actually connecting with the customer.
  2. Share the agenda. “Give the structure of the conversation and context around what their expectation should be.Jump into why, what your pitch is going to be, what they need to understand, and educate about the problem that you try and solve.
  3. Establish credibility. “Contextualize the value and identify the KPIs they’re going to measure success by when they do actually buy your product.”
  4. Map your close and confirm and schedule your next steps.

Pitch. Here you’re making a formal pitch for the product. Sales gives these top tips:

  • Make it relatable. “They have to understand it. In the VC community, a lot of people did the X of Y [i.e. ‘The Airbnb of video equipment’. A lot of VCs don’t like that anymore, but it’s the way that they were used to relate to certain products — you can learn from that.”
  • Pause for questions after you give a pitch. “Your pitch is your initial story or value proposition. Pause and give them an opportunity to actually engage with the conversation, because there might be an objection that they have.
  • Try this script: “One of the things I always say is, ‘I love to hear myself talk, but it’s more important to actually hear what you guys have to say. If you guys have any questions, I’d really love it if you’d raise your hand and interrupt me, because I’d actually love to hear what is resonating with you and what’s not and how I can actually make this more valuable for you.’”
  • A script for large groups: “I’m going to be pausing for questions after each section, or after each slide. If you have questions, I would just ask you to write them down and I’m going to pause after that and ask any questions. If, at any point, you have something that’s really important before I move on, please stop me and feel free to ask a question.”
  • Pause after your ROI story. “You basically can tell whether your value proposition and what you’re trying to sell lands at this point. It’s a really good place to pause. They’ll either engage or they won’t. If they engage, they’ll engage around how to implement and process oriented questions. Or they’ll give you an objection around whether the product is a good fit for them or the value or ROI that you’re saying whether they believe it. At least they’re giving you that information. If they’re quiet, that’s a problem.”

Demo. Do your demo after you’ve discussed customer use cases. “At this point you’ve validated that you do what you say you can do. Now you show the product on how you can do it.” Tips:

  • Focus on three key areas that apply to the customer. “Only three areas. You don’t need to go into the entire product. I know as founders we are all in love with our product. It’s a wonderful thing, but focus on the key areas and why the customer’s going to buy. Don’t dive into anything else, because it’s just going to cause problems. You get in the weeds.”
  • Preempt their objections. In qualification, you should have unearthed their problems as well as a sense of what their objections to your product might be, whether that’s cost or how a certain feature will fit with their needs. Use that information. “If you know there are objections that are likely to come up with that particular customer, use your use case and how you talk about your customer to handle that objection.”
  • Map the close. “You should know what’s going to happen when you get off the call, when it’s going to happen, and who with, and three steps ahead of that. Because that’s how you’re going to tighten those sales timelines.”
  • Protip: Sales uses the sales frameworks BANT or CHAMP to map her closes. A good map to a close will answer important questions like:
  • How is budget going to get allocated?
  • Have they spent money on this type of problem before?
  • What would that process look like?
  • Is the budget time or money? If you have any type of implementation, that time allocation is actually the bigger budget.
  • When do they have time?
  • If it’s a development tool, are they on sprints? What do their sprints look like? How do you get something into a sprint?
  • Wrap up demos with a next step. “Don’t get off the phone without a time on the calendar. Even if they’re not willing to put a time on the calendar, put a time on the calendar for a check in,” Sales says.
  • Make sure that they have homework and you have homework. “When people complete your homework, you know that they are taking incremental steps in the buying process. On average, to get to a close, there are going to be investments that are made on their end. It could be an NDA or getting another person involved. Know the next steps and state them.”
  • Set the agenda for the next meeting. “Clarify your steps and your steps before you get off the call and make sure you’re clear on those and what’s actually going to happen.”

Close. Sales has one key tip for closing: Always wear a value hat. “The always be closing mentality is more of always have a value hat on than an always be closing. One thing, for example, I’ve tried to do throughout my career is I’ve always tried to find ways to help people. That’s what I try and close them on is how can I help this person? Can I make an introduction? Can I do something for them? It comes back,” Sales says. “Closing can simply mean that you’re helping people.

“Handle the objections you know are coming by adding them into the use cases. That way, you’ll have a story that shows how you solve the objection.”

In Conclusion

Everyone has their own style and voice of selling. It may be to develop a friendly rapport, or to be direct and metrics-focused. Make a real, human connection. Ask smart questions. Prepare — have questions and answers ahead of time, but also know how to read the room. Back off if the product isn’t the right fit, or break the ice so that folks feel comfortable interrupting you to ask questions. Do your research and use questions to query the customer’s needs, decision makers and pain points. Keep in mind that you’re always working to be helpful to others — it’s not about you, it’s about the customer. And finally, remember that while these are strong guiding principles, how you execute is ultimately up to you and has to work for you. “There is no one right way to sell,” Sales says. “Find out what’s right for you.”

Watch Whitney’s talk from our Scaling Sales event at Spero Ventures



Spero Ventures
Spero Ventures

Spero Ventures is an early-stage venture capital firm driven to deliver value to shareholders and society.