Going Upstream – How to Recruit and Develop for More Complex Sales

complex sales

SMB sales organizations, that are growing their product and average contract value as a basis to go upmarket, inevitably face the talent challenge of needing reps who are capable of running a strategic selling process. Often, due to budget constraints and many other factors, many organizations can’t afford to bring in experienced strategic sales people (ie. enterprise) so they have to hire inexperienced talent who have the potential, or train their existing SMB reps to move upmarket.

In my prior sales leadership roles at places such as IntraLinks, Undertone and Trustpilot, I’ve found that while it is challenging to train a sales person to do strategic selling in-house, if you find new or existing people with potential, great things can happen around their development, even if originally they were hired to do SMB sales.

We’ll go over what I look for in the interview process when considering these profiles, with a focus on raw skills as opposed to experience and then what I do in training to help them become successful.

What I Look For

1) Ambition

I look for a clear vision of where they want to go in their career. I don’t care if they just want to increase earnings through quota achievement or if they want to move into management down the road, I just care that ambition is demonstrated as a basis for achievement.

2) Desire

I look for high level of passion and willingness to run through walls to be successful. While its difficult to screen for, I am essentially looking for a person who will optimize every opportunity and push every individual sales conversation to the end level. Passion and willingness to do the extreme is typically seen in someone who is a life-long learner and wants to constantly improve.

3) Attitude of Hating to Lose

Ignoring the age-old debate between “Loves to Win” vs. “Hate to Lose” for a minute, I’ve found that someone who has a strong feeling on winning or avoiding losing is equally important, more importantly, in how the feeling drives them. I care to see that they have reflected on their mistakes and losses and they learned something from those instances. I typically have them talk about specific examples as a way to screen for humility, and how they incorporate new learning and feedback into their craft.

How I Assess Candidates

Ability to operate both strategically and tactically.

I’m actually okay if they don’t have a fully developed strategic mind, but I’d like to see how strong they are, tactically, to offset that development area.

  1. Strategy: I define their strategic thinking as their ability to create a repeatable plan to learn about an enterprise, analyze a market, and work with a variety of departments in order to get a deal done.
  2. Tactics: I look for their tactical understanding of sales, on how activity, sales process cadence, and deal-level conversations can help them move a deal forward.
Ability to build champions externally and internally.

I believe that in complex sales cycles, a great seller can be in the driver seat of success by building champions externally, but also critically, internally. Particularly in early and mid stage startups, I’ve found it key to hire someone who can marshall internal resources (ex. marketing, ops, product, legal) to help them close deals. Many people are competing for the same corporate resources to get things done, successful reps know how to get everyone working for them.

Depth and clarity of their sales process.

I typically ask reps to walk me through their sales process and then dig in with a lot of follow up questions. I’m trying to understand how deep they can go in explaining their sales framework, how they troubleshoot deals, and their general organization routine. Ultimately, I’m trying to ascertain whether their success was random or a byproduct of great work habits, strong understanding of their industry and a mastery of basic sales fundamentals.

How I Train Enterprise Sellers

Training a seller to pursue a 9- month sales cycle is very different than the one call closes and monthly sales cycles they may be used to. Broadly speaking, transactional selling is more activity based and metrics driven because sales stages are short, so success is more measurable and linear.

Enterprise sales is generally harder because it requires understanding a broader set of inputs of an organization, navigating a diverse set buyer personas, overcoming more hurdles, how value/ROI is interpreted, working a timetable, and needing to address direct competition to get a deal done. And of course, even when a deal is done, there are still downstream execution logistics which requires an understanding of how to navigate legal and procurement to get the contract signed, not to mention actually integrating the solution into the customer’s enterprise infrastructure.

One of the primary ways I build a basis to train sellers to operate within a structured, enterprise sales framework is using Account Plans. An Account Plan is a document that encompasses the research, thinking, and planning of an individual seller against a targeted prospect or customer.

Building a great Account Plan is itself great training for a new enterprise seller and I’ve even found it a useful for transactional sellers who have longer sales cycles. It requires them to conduct a huge amount of research on the company including: key people in the organization, revenue dynamics, strategic priorities, and how the company fits into the broader industry landscape. The enterprise seller will then need to tie all these learnings back into a selling strategy they can break down into tactical steps.

I’ve used great Account Plans that are simple, single page word documents and sometimes I’ve seen 10 tabs of a complex excel spreadsheet detailing all the permutations of contact strategy and various buyer personas. One thing I’ve noticed is that great enterprise sellers can create a custom Account Plan autonomously, writing down the scientific method in which they would approach a prospect or customer without a lot of supervision.

Here’s a sample Account Plan Template to get you started.

Final Words

I’ve seen both individuals and companies think about moving to enterprise as a right of passage. It can become a weird obsession that does not play to the strengths of the sales rep or company.

Many sales reps are better suited for high velocity, transactional sales because they enjoy fast stimulus and the ability to get predictable results from pure effort and activity. In those cases, I always recommend the person to think hard about why they want to move to Enterprise sales in the first place, and whether they will truly be happy once they get there.

Similarly, for many companies, pre-maturely selling their product into the enterprise can deplete and stretch their engineering and marketing resources as they are forced to compete against a broader set of features and products. If they don’t navigate upmarket with a thoughtful product and sales talent strategy, it can actually be a huge detriment to the organization.

Fred Mather is a consultant at Aqueduct Advisors, a strategic CRO consulting practice helping early and mid stage companies scale more effectively. In his previous roles he served as the Chief Commercial Officer of AutomotiveMastermind and General Manager of Truspilot.