February 8, 2021

When Should A Startup Consider Sales Training?

When building an early sales team, startups can either hire “the best”, or hire high-potential employees who, when provided with great training and coaching, can become “the best”. It’s highly unlikely that “the best” will work for $1X0 on-target earnings + 0.X% equity, so the latter is the only option most startups have.

This article scratches the surface on what skills startup sales reps should be expected to have or quickly acquire in order to become top producers. Based on the large quantity of skills and their associated depth, my opinion is that sales training should begin the minute the first person is hired to speak with prospects. It would be great to hear your views after reading the following sections.


All salespeople, from sales development reps to enterprise field reps, need to be product experts. If someone doesn’t know what a product does and how it specifically applies to customer pain points, how can they be expected to close deals? Even if they do close a lot of deals, how much more would they close, given better product expertise?

One way to test someone’s basic understanding of a product is to have them do a “whiteboard demo”. In this exercise, they literally draw a demo, screen-by-screen, feature-by-feature, on a whiteboard. If someone can complete this exercise, they know the product.

However, good demos don’t just focus on features; they focus on how the product can be used to create value for the prospect. Specifically planning and dynamically adjusting demos on the fly will allow a sales rep to create a hyper-relevant experience for the prospect and keep them engaged.  


Knowing the target market inside and out will help salespeople have strong, relevant conversations with prospects. At a minimum, salespeople should be experts at:

  • Prospect Personas: For each persona in the target market, what they do all day? How is the product personally relevant to them?
  • Competition: Who else does what, and what are key [real] differentiators?
  • Culture: How are decisions made by prospects in the target market? What scares off prospects?
  • History: What vendors have come before and how have they succeeded/failed? Repeating a previous vendor’s mistakes will kill a sales rep’s credibility instantly.

Sometimes salespeople think they are doing valuable work by asking questions, regardless of the questions they are asking. If someone can Google the answer with a high probability of success, don’t waste the valuable time with the prospect on these basic topics. It’s critical to know the basics in advance and spend valuable prospect-facing time on items that can only be learned in conversation.


Early stage startups likely won’t have a repeatable sales process. Rather, they will be experimenting to figure out what will be an effective and repeatable way to sell the product.

While at various stages in the sales process it’s not clear what should happen next, it’s probably clear what COULD happen next. For example, after an initial demo, the next step might be:

  • Another Demo to a different audience
  • An on-site workshop with a real-life customer use-case
  • An intense Proof of Concept
  • A proposal that omits the steps above

Just because a company isn’t clear what a repeatable next step will be at every stage of the sales process, their sales team should be armed what all the options that could come next, and messaging to drive the deal in the right direction. Without a strong plan, they might mismanage and lose high-value prospects that would otherwise close.

One could argue that due to the uncertainty, strong sales training around process is MORE important before achieving product-market fit.

Sales Tactics

There are several sales tactics that range from absolutely critical to helpful advanced topics, such as:

  • Qualification: Understand the prospect’s need, budget, decision process, timing, etc.
  • Pipeline Management: How to efficiently and rapidly move deals along.
  • Email Skills: How to get someone to open and respond to emails.
  • Phone Skills: Engage prospects and get them to open up on the phone.
  • Objection Handling: Know every objection in advance and have a thoughtful way to handle them. Know that being defensive doesn’t work.
  • Soliciting Feedback: How to get a prospect to open up and honestly discuss their opinion.
  • Lost Deal Analysis: When deals are lost, why, and what tweaks can be made across the company?

There are tens, if not hundreds of additional sales tactics which are learned as people advance in their sales career. Why not learn them early on instead of waiting for an opportunity to pop up?


Knowing how to work with other departments might not be at the top of the list when it comes to closing specific deals, but it’s a critical skill when it comes to building a strong company. Some examples of why it’s important for salespeople to work with other teams include:

  • Product: How are bugs and feature requests reported? What is done with general user feedback?
  • Marketing: What’s working and what isn’t? Based on prospect conversations, where might marketing focus to improve the quantity and quality of leads?
  • Customer Success: What can be done in the sales process to set customers up for smooth onboarding? What should be avoided?
  • IT: What productivity tools are available and how can they help improve the sales team’s performance?

Strong teamwork enables companies to get more done with less friction. It is also an excellent way to develop future leaders internally.

General Business Skills

Employees from different backgrounds have varying skill sets, and this diversity is great when building a well-rounded company. However, gaps in skill sets can potentially be devastating to an employee and cause them to lose the respect of customers and/or co-workers. Some examples of general skills that startup salespeople should master include:

  • How to say “no”: When prospects or managers make unreasonable demands, how can the situation be handled?
  • Spreadsheets: How to manipulate data efficiently to answer questions and present results.
  • Managing up: It’s especially important in startups to articulate advice to executives regarding what’s happening in the market and proposing ideas to improve operations.
  • Accounting: At a minimum, understand financial statements and how they relate to a prospect’s decision process. Also, know basic terms such as accrual.
  • Legal: When might prospects push back on a contract and what is an appropriate reaction?
  • Whiteboarding: Be able to articulate complex ideas elegantly via a whiteboard.

Like sales tactics, there are tens or hundreds of more skills that are likely relevant to a startup salesperson.


Once a sales team starts to find its repeatable process, it then begins to scale. Without prior knowledge of what scaling looks like and how everyone on the team will be impacted, a constant state of confusion and firefighting could erupt.

Sales reps should spend very little time thinking about scaling in the early days, but they should realize that things will continue to evolve until a repeatable process has been solidified.

Final Thoughts

There are hundreds of topics that must be mastered for a startup sales rep to truly excel. It’s easy to say “hire the best and let them perform”, but “the best” probably aren’t willing to work in an individual contributor role for what an early-stage startup is willing to pay. However, there are a lot of great people with high potential who can become “the best” with some excellent training.

Follow Cory Bray and Hilmon Sorey on LinkedIn.

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