15 Critical Questions for Selling at a Startup

Learnings from high growth companies

First, a little background here and where these questions originated… In late 2008, I became the first quota carrying sales rep for Acquia. We were around 15 people and it was 1st job out of college. Acquia was an unbelievably exciting startup to join, but I was terrified— I had a quota with a new product and had to land our first clients. It was obvious Acquia had potential, but had no idea that Acquia would become the fastest growing private software company in the US with future plans to IPO. I’m fortunate to have been able to work and learn from some of the smartest business, technology, and sales leaders there. 5 years (2 of which were in Oxford, England, starting the EMEA sales team) were pure hustle. Long story short, I ended up figuring out the sale and averaging 150–200% of my quota and was consistently a top producer. Burnout led to traveling and after backpacking for nearly 1.5 years in Asia, I worked for Influitive (another high growth startup) and now advising & building the sales process to help get another early stage startup, Outlearn, get off the ground. It’s gotten me thinking about what knowledge, questions, and answers we need to develop in sales to sell effectively and inspire prospects. To learn from previous sales and startup successes, I asked myself:

What are the key sales questions for a startup and sales to answer in order to effectively sell and scale fast?

I believe the questions below are critical for selling, scaling, ramping new sales hires, and ultimately understanding how to build + scale sales. Too many times new sales reps are left with a pile of PDFs with features, benefits, and case studies. It’s not enough. There really needs to be a structured way of helping each person ramp and sell effectively with the right knowledge. What is the right knowledge? What questions do you need to ask yourself and why? Figure these questions out as fast as possible. Build hypotheses for them. Test. Measure. Ask your clients — why did you really buy? It’s likely it may be different than what you assumed. Determine how you will know if you hypotheses is right. Keep testing. Keep learning. Keep asking yourself these questions.

1. Why was the company founded?

The story behind why it all matters

This is all about inspiration and beliefs. People identify with beliefs and when you can uncover that commonality, it’s much easier to build a relationship. For example, Outlearn believes that there should be an easier way for developers to learn and stay up to speed on new technologies, up-skill, and be able to more effectively share knowledge with the rest of the engineering team. Outlearn explains the why nicely in their Professional Developer Learning Manifesto:

We’re calling it. Professional developer learning in most organizations is broken. The default approach to learning — “just figure it out on your own” — wastes millions of hours of productive work. It’s totally medieval. As a tech community, we can do so much better. Let’s fix it.

We’ve collectively spent three decades delivering successful software platforms. We’ve spent the last year intensively talking to hundreds of developers and managers about how developers get hired, stay hired, and become successful. It turns out that learning is important to developers the way swimming is important to sharks — they have to do it to survive.

2. What does your ideal customer look like?

Not only who to sell to, but who benefits the most

You can’t hunt effectively if don’t know who to target. This is also important because it helps you figure out your TAM — Total Addressable Market. If there aren’t enough of your ideal customers, then you’ll likely need to move into other markets. Wrong fit customers also equal higher churn. It’s gotta be a win-win and not just about closing a sale. A good fit is critical for a successful relationship. Harvard Business Review’s “How To Identify The Best Customers For Your Business” provides a process for evaluating the range opportunities you may have.

Many companies pursue growth opportunities without adequately defining who their ideal customers are. That lack of clarity can hamper profitable growth.

3. What problem or pains are you solving for?

Technical, Organizational, and Personal

An obvious one. But, sometimes more difficult to answer than you think. Something needs to be broken or you need to be doing something 10x better than the incumbent tool, service, or company. Personas plays a big role in “what problems are you solving?” question. The VP of Engineering is looking to solve different problems than the Development Manager. They care about different things and your value proposition needs to correlate in conversations. There’s 3 different levels of pain and these will give you insight into the reality of a deal happening. How do you plan to solve for pain at each different level; technical, organizational, and personal. OpenView Venture Partners has an excellent post on this: “Sandler Selling: The 3 Levels of Pain.”

Simply put, a potential buyer who has a personal investment in the problem being resolved is far more likely to “walk side-by-side” with the seller throughout the sales process. As noted in the first article in this series, that commitment is really one of the primary goals of the Sandler qualification process.

4. How are people solving the problem today?

It’s all about understanding & empathy

Understand your customers and prospective clients. Being able to empathize with their situation wins big points. It also shows them that you understand their world and why the pain matters to them. Empathy helps build the relationship. You and the client should be on the same side of the table working towards a mutual goal. Most importantly, you can’t show them what a change or their future state would look like without understanding their current situation. Are they actively try to solve the problem? One of the questions we always got asked at Acquia was:

What happens if they do nothing?

5. How do you solve the problem differently?

Deliver insight and add value

People crave insight and a better understanding of the world around. Especially, if there is a problem that they don’t understand how to solve. Providing insight throughout a sales process makes you a valuable source of information. It makes people want to come back and connect with you again. Ooze insight. Articulate why your solution is the way it is. What makes it so compelling to switch or to purchase. How is it 10x better than what they’re doing today? Ben Horowitz explains this well in his book “The Hard Thing About Hard Things: Building A Business When There Are No Easy Answers”:

Build a product that is 10x better than the competition. 2-3x isn’t enough to get them to switch…competitors won’t sit by and watch you take market share. You need to get it and hold it ASAP.

6. How will the service dramatically change your customers’ world / way of doing things?

Paint the ‘before and after’ picture

Some prospects have a particular goal in mind — A desired future state. Others don’t. In both cases, you can influence what a better future could look like, and it becomes your job to paint that vision for them. At Acquia, we created project plans as part of the sales process to show people how we get from point A to B. We told countless stories of the before and after of client successes and in detail of how we got them there. Helping clients understand each step helps reduce risk and makes it easier for them to buy. People are constantly striving to improve their own world — show them how you help them do it. The more they can imagine how their life and way of doing things will change, the better.

7. What are relatable customer stories that prove your service and can be repeated?

Evidence that hooks your audience

Stories that are vivid, relatable, and with actionable insight. Why did they come to you in the first place? What was their situation and how is that similar to the prospect’s situation that you are talking to? Being able to make these comparisons help the prospect form a bridge in their minds of how you’re going to be able to help them in the same way. Fast Company has an excellent post on this “3 Ways To Tell Better Stories and Make People Care”:

GOOD STORIES MOVE YOUR CUSTOMER, CREATE LOYAL FOLLOWERS, AND HOOK YOUR AUDIENCE TO PLEDGE THEIR ALLEGIANCE TO YOUR BRAND. HERE’S HOW TO WRITE SOMETHING THAT PEOPLE WILL ACTUALLY WANT TO READ.

8. What will compel your prospect to keep coming back?

Become a source of valuable information & insight

This is all about being able to add value at every step of the sales process. You can’t sell unless people want to engage and have a reason to keep coming back to you. I’m not convinced sending case studies as an attachment to your email is adding value. No one has time to read it. Summarize it for them. Include interesting articles that aren’t your company blog posts. Make an introduction to a partner or someone who can provide them with additional insight. Create deliverables (from both sides) in the sales process so you can continually learn about your customer’s situation, but also take that information & data and continue to provide actionable insights to them. Help them do their jobs better. Make them more successful.

9. Why did your existing customers buy?

Dive deeper for the real reason

“Oh, they wanted more case studies & references.” No, it’s gotta be deeper than this. “Company A bought because they are in the process of making a big shift from on-premise contracts to offering SaaS products. They can’t use the existing bulk of their customers as references because they’re using different products. They are crossing a different chasm. There currently aren’t enough references to meet all of the sales’ reps requests. This is putting significant revenue at risk and hurting the team’s ability to effectively sell. We’re behind on our sales number and need to close X deals before 2016.” Dive deep into the story. Ask your customers after the sale. Understanding the why will help you make more effective business cases to your next set of clients.

10. What’s your best business case?

Always develop with the client & get feedback

A business case is not a regurgitation of marketing collateral and positioning. It needs to articulate how you get customer from point A to B and the benefits they’ll receive afterward. How do you justify the cost? Why now? What happens if they don’t do anything? Ultimately, asking for your colleagues business cases will help you fine tune yours and craft stronger arguments. It’s something that should continually improve over time. Always develop the business case with your prospect. Otherwise, how do you know you’re not just shooting in the dark?

11. What are the top objections that I’ll face?

Don’t just answer the objection, understand its origin

What are the top 5 that come up and how do you proactively over come them? Tackling these before they even come up in conversation is even better. There’s usually a small number of people on a team who handle these exceptionally well — seek them out and learn from the best. If you’re one of the first sales reps, then you’ll need to figure this out — do it as a collaborative effort with other members of the leadership team. They’ve likely been thinking about these for a while or since they started the company. If you’re later stage, you can look back at your losses to uncover common themes. Looking for other tips? Check out this excellent post on SalesHacker.com: “10 Tips For Getting What You’re Worth: Negotiation & Objection Handling in Sales.”

Never answer a question without understanding the context behind it.

12. What were the compelling events that propelled the deal to happen in a predictable and forecastable way?

Figure out ways to create urgency

Compelling events create urgency. Urgency gets people to move faster and gives them a reason to do so. If you know what the typical events are, then you can ask, uncover, and incorporate into your sales process with a timeline of what needs to get done by when. What happens if they don’t move forward? There’s gotta be some level of consequence for not moving forward now, otherwise it’ll be really easy to push you off indefinitely. Compelling events are all about moving you up on the priority list. A HubSpot blog post explains what to do if you don’t have a compelling event:

If the sense of urgency doesn’t exist, then you may need to challenge the prospect on what other initiatives are more important. You may even need to switch over to a provocative sales approach if you think the prospect is focused on the wrong priorities.

13. How do you create the best customer experience possible?

Don’t stop at the sale, continue building the relationship

Customer experience is the ultimate competitive advantage. It starts with sales and continues with the ongoing relationship. Being able to explain how you will work with them helps people feel comfortable. Knowing what to expect reduces the chance that your customers will feel disappointed while helping them to understand how to get the most out of your service to be successful. This should never stop. Building the right relationship through customer experience is incredibly valuable. Driftt explains this really well in one of their blog posts, “Relationship Marketing: Why Marketing to Customers, Not Strangers, Is The Future of Marketing.”

And valuable is not just a buzzword — a five percent increase in customer retention can increase a company’s profitability by 75 percent. Or to break it down even more: renewing a happy customer on average costs just 11 percent of what it would cost to acquire a new customer.

14. How do you harness your current customers to help you land more customers?

Happy customers are usually willing to help you with referrals

Peter Drucker once said “The purpose of a business is to create and retain a customer.” I believe today’s version of this should be “The purpose of a business is to create and retain a customer that introduces you to more customers.” Your customers are your most valuable asset. They be a huge source of new revenue growth. Why? 84% of B2B buyers start their buying process from referral. Referral leads close faster and typically add more value to your business. Mastering the customer relationship and experience can unlock this potential. According to the Journal of Marketing, a referral customer has a 16% higher life-time value.

Using information from a database of 10,000 customers acquired by the bank in 2006 — about half of them through the institution’s referral program and the other half through traditional marketing efforts such as direct mail and advertising — the study tackled three questions:

Do referred customers have higher margins than other customers?

Do referred customers stay longer with the firm than other customers?

Do referred customers have a higher customer lifetime value (CLV), the net present value of all the profits a customer generates over his or her entire association with the firm?

The answers, according to the study, are all positive.

15. Why are you passionate?

Everything else won’t matter if you don’t have a good answer

Purpose and passion driven sales people will outsell those who aren’t. I’ve been on both sides — I went from top rep at a company to being the next to the last rep. The passion & purpose weren’t there. However, I’m fortunate to have recognized this and have made changes to get back to the things I love doing — building something from nothing off the ground. It might be one of the most important things I’ve learned in the startup world. Why is passion and purpose so important? The reason is quite simple and Tony Robbins said it was the best advice that anyone has ever given him:

Find a way to do more for others than anyone else is doing.

Passion and purpose naturally compel you to help others more. Simply because you care more. People feel the difference.

Before anything, take some advice from one of the most respected executives, Jeff Weiner, CEO of LinkedIn about what you need to ask yourself everyday…

And it’s amazing to me how often I’ll sit down with someone who’s five, seven years into the throes of their career and they’re not happy, and what’s happened is they’ve been swept up in a stream of opportunism, a hot job, or a promotion, or more money, as opposed to taking the time to ask themselves what it is that they want to do.

What is it that you ultimately want to accomplish?

If you enjoyed this post, then check out “Job Hunt vs. Purpose Search” — why you should be hunting for a purpose, not just a job.

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