Experience Series: Sales

Brandon Dixon
11 min readNov 1, 2019

This post is part of my Experience Series where I share opinions I have formed from building companies and running product. Each posting is a break down of a company function. This post focuses on sales specifically.

General Opinions

It’s easy to “show up and throw up” on a demo. That’s not doing sales, that’s you talking the entire time. Do prep work prior to meetings, have a plan and spend as much time as you can doing discovery with the prospect.

  • During the early days of PassiveTotal, we were proud when we managed to get our product pitch down to 45 minutes. These days, I won’t even open a deck unless proper discovery has been performed and there’s a clear need for the product. Respect your time, and the time of the prospect.
  • Looking back, we spent so much time speaking and not enough time listening. Prospective customers will happily tell you all the ways their existing solutions don’t work or the challenges they face or what their boss has asked them to do. They can’t do all that though if you are spewing your pitch. Ask good questions and align the answers to your solution’s value.
  • In terms of prep work, you should know who you’re talking to––their work history, how they fit into the business, who their manager is and who their peers are. You should have a set of discovery questions you can ask to uncover pain points, understand the team and direct the conversation towards your product. Finally, you should have a way of taking notes and being clear on action items.

Define a set of sales stages as best as you can. There’s resources out there to help here, but you want to ensure you are able to track progression of deals. Not every lead is an opportunity.

  • Sales is a nuanced process and is not simply “sold” or “not sold”. As you enter an account, it naturally works through stages like “first meeting”, “product pitch”, “budget identified”, “price shared”, “trial started/completed”, “procurement approval”, “purchased”. Reflecting these stages lets you better track where you are in the purchase cycle and likelihood the deal will close. If too much time passes, it’s best to make the hard decision and remove the deal from your pipeline.
  • When we first started out with PassiveTotal, we had no clue that sales cycles would last anywhere between 3 months all the way to 9 months. There’s a whole lot that happens between your technical champion saying they want to buy your product and the organization actually signing off to purchase it. And even then, you still need to wait for your money.

If at all possible, use metrics and happy paths as a means to score leads or help auto-progress deals through stages. This will save you time and help you focus on which accounts to target.

  • PassiveTotal was a freemium platform and so we were seeing new users register every day. If we tried to pitch every single user who registered, we would have never gotten anything done. To help separate the signal from the noise, product metrics and user data (company size, industry, etc.) were factored into our lead sorting. Active user part of an established organization targeted by threats? Engage.

If your product allows for prospecting, go for it. A great way to start a conversation is to show the prospect something about them that may peak their interests.

  • You should really know your audience before going down this route. In PassiveTotal, our users tend to value their privacy more than a normal user and do not take kindly to random contact from a vendor. This is the opposite case in NinjaJobs though where someone is always willing to engage with someone interested in helping them find a new job.
  • If you decide to engage, show up with something worthwhile––again, respect the time of your users. If someone just downloaded a recent whitepaper from your website, ask them what they thought of it or what had them interested in that sort of topic? Reaching out and immediately going into pitch-mode is unlikely to be successful.

Respect your buyer and their time. Don’t be late, come prepared and follow-up once you have had the meeting. This goes for post-sales too.

  • Follow-up can’t be stressed more. If you say you are going to do something, do it. Unless you have a product that’s absolutely needed by everyone, it will always be up to you to prove your value in order to move the deal forward.
  • I recall being on a tropical island for a conference and speaking with one of my clients from NinjaJobs. They made a side jab that I was here having fun while their job post was having issues being displayed. It was so embarrassing to hear this. I immediately left, went to my room, identified the issue, fixed it and pushed it live to production. If someone is paying you money, you owe it to them to ensure the product works.
  • When’s the last time you attended a meeting and thought to yourself, “I wish that person spoke longer”? Chances are high that’s never crossed your mind and those you pitch are likely the same way. Be crisp, get to the point and avoid a bunch of fluff.

Opportunities open more than 90 number of days without progression should be closed and considered stalled.

  • Never aging out opportunities just leads to a messy sales pipeline where you can’t reliably predict what is likely to close. 3 months with no interactions or progress is the sign you are dealing with the wrong person inside of the account, you have not shown value or what you are aiming to solve is not a priority. Add these leads to your marketing nurture tracks and move on.

Use a CRM (Salesforce isn’t the only solution) that has a good API, flexible data model and ideally auto-populates details about contacts.

  • Before PassiveTotal released an enterprise product, we had decided to wire in the HubSpot’s CRM into our platform. Registrations, logins, activities and marketing were all tracked and associated with leads in the system. This simple concept allowed Steve and myself to really scale the business with only two people. Each day, we each reviewed our queues of activity––me on the product usage side and Steve on leads and opportunities. Another benefit to HubSpot was their email tracking plugin that would associate actions or follow-up activities directly to the lead in the platform.
  • With NinjaJobs, we had a slightly different set of requirements for our sales process in that we needed to support a team of recruiters and the ability to search across resumes. After doing research, I identified CATSOne and wired that into our platform. CATS operated as the NinjaJobs recruitment database, but also generated job orders and tracked platform activities so our recruiters could find the best people for the open jobs.
  • HubSpot has since changed their license model. If I were to do another project today, I’d likely use something like FreshSales, Prosperworks or HubSpot––essentially any platform with an API and way to automate the mundane portions of sales.

At least once a week, analyze the new users inside of your product and figure out who they are. Do they meet your expected audience? Where are they coming from? Are there any patterns in users?

  • Once a day makes more sense, especially when the company is smaller. If you don’t find yourself addicted to the running list of new users entering your product, you may want to reconsider if a startup is the right place for you.
  • Each day, PassiveTotal brought new users into the system from all different parts of the world and from all different types of companies. Using Google Analytics and social media tracking, we were able to identify key channels for getting new users and then formed marketing plans to invest more into those channels. Sometimes these efforts failed to get the traction we wanted, but we always learned from the process.

Word of mouth is the best way to enter an account. Make it easy for your product champions to invite their peers or share elements of your product.

Procurement is tough no matter who you are. Expect the process to take a long time, especially if you are a nice-to-have product. Keep in mind, you will need to support the user during this process and can’t easily just nuke their accounts.

  • In the early days of PassiveTotal, procurement wasn’t really a known term to me. As our first deal neared closing, I got a big dose of reality in dealing with the procurement department. More discounts were needed and more justification had to be provided––something we did not plan to for at all. I now know that it’s okay to ask about procurement with your prospect. If they want the product, they may have an idea of the internal sales process or what to expect as paperwork moves through the organization. Take any advantage you in the account.

Know your audience and have clear goals. If you are speaking to technical users, chances are high that they do not have the budget. Your goal is to get them to help you convince their manager to buy your product.

  • Even when you build strong technical champions, it can be tough to get them to make the case to purchase your product. Align yourself to their goals and even go as far as getting an introduction to their boss or decision maker or helping them craft a message to those individuals. The less work they need to do, the more likely they will help you out.
  • There’s been a few times with PassiveTotal where I have generated a “canned” email highlighting all the benefits of our platform and how it was superior to other solutions in the market. Attached to the email was a data sheet describing the solution for more detail. When I get the sense that we need to prove ourselves in an account, I will pass this email along as fodder that can be used to convince upper management. Sometimes it works, other times it doesn’t.

Influence is not budget. People who say they have massive influence or a silly budget figure probably don’t.

  • People like this are in their own class of “interesting”. Without elaborating too much, you will know when you come across one and it will be pretty clear they are going to be a waste of time. Be nice, move along or more importantly, get introductions to other team members or departments.

Once you land in an account, let the product do the heavy lifting, but keep the relationship alive. Provide timely support, follow-up with status checks and keep an eye on your users to see if and when they change roles or companies.

  • At RiskIQ, we call this Customer Success and no matter what you name it, this function is difficult. Getting through the sales process can be a slog, but that’s just the beginning of the customer journey. Once sold, you need to ensure your product is being used and that your users are seeing value. When I say “heavy lifting”, I mean making use of metrics that indicate usage––login, activity, happy-paths, growth, etc. If you notice a decline in any of these values, it’s worth having a meeting to engage the account and ensure it’s healthy.
  • There were times in PassiveTotal where a bug would be surfaced by a client and I would fix it within minutes. To the customer, this was as close to magic as you could get and it created life-long product champions. Naturally, this cowboy-style coding does not scale as you get larger, but when you can, it’s awesome.

Taking money for your product changes your relationship immediately. It doesn’t matter if the buyer is a friend or not. Be professional and deliver their service.

  • Your early buyers are likely to recognize you are a startup and may run into delivery issues, but minimize this as much as possible. Throwing a price tag on your product implies you’ve went and done the necessary testing to know it will scale to demand or function properly 100% of the time. If that’s not the case, consider delaying your launch.
  • Some of the harshest product feedback I have gotten to this day comes from friends or peers in the industry. While it hurts sometimes to hear, those are some of the same people I call up when I want to test a new idea or get an honest answer to a question. Develop thick skin and expect to get an ear full if you don’t deliver.

Let your friends or peers off the hook when you see them if they claimed they would buy and didn’t. It’s an awkward situation and one they likely have little control over. Best to not hold a grudge and preempt their apologies.

  • I’ve mentioned this in other points in the series, but this behavior ties into people largely being nice and wanting you to succeed. Try not to get sucked into the hype generated by peers and use metrics to evaluate your sales/marketing/product progress.

People love to talk, so let them. Learn from your prospects and customers — their problems, their organization structure, how their funding works, which competitors they use, what they think of other products, etc.

  • The more information you have about an account, the market, or your competition, the better. All of this helps you in your sales process and allows you to start building a repeatable process to counter objections, pitch efficiently and get introduced to the budget holders faster.

Use a CRM or integration that allows you to associate email correspondence to your contacts. As a bonus, integrate your calendar as well, so you can see when you had a meeting.

  • When we started PassiveTotal, HubSpot was our tool of choice. After being acquired by RiskIQ, we switched over to Salesforce and their plugin tools.
  • For meetings and conferences, I’ve had the best luck with Zoom so far.

Your email send-to-recieve ration is going to look something like 90% out and 1% in. Every week, sit down and identify previously sent messages that got no response and try again.

  • This goes back to following-up and it’s tough. Your days will easily turn into a blur where the email you sent two weeks prior feels like it was only two days ago. Reviewing your sent messages or leveraging plug-ins/email clients that can remind you of one-sided conversations go a long way in ensuring you are always keeping the conversation going.
  • With PassiveTotal and NinjaJobs, we were able to automate some of the first few emails to an account. This saved us a ton of time and helped filter out anyone who may not be as serious about upgrading. By no means did we give up on anyone who didn’t respond, but we did factor it into their likelihood of progressing in the sales cycle.

Order of prospect outreach communications by preference. Call. Call again. Email. Call next day. Email a few days later. Get creative.

  • If you don’t like being on the phone or giving the same pitch over and over, don’t go into sales. You need to get used to being rejected, ignored, yelled at, misdirected, strung along, and chastised. It’s a tough job and it takes real persistence. With that said, next time a sales person calls you, consider being direct with them and treating them with respect––they are human just like you!

If you’re going to do a demo, make sure there are no bugs and have a video back-up. For the materials, try to personalize the content, but at the very least, ensure it’s not older than 6 months.



Brandon Dixon

Founder of @BlockadeIO, PDF X-RAY, and @PassiveTotal. Partner and developer for @TheNinjaJobs. VP of Strategy for @RiskIQ. Roaster at @SplitKeyCoffee.