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Optimum Talks Blog

Your Next Sales Leader

by Santino Pasutto
July 22, 2020

Start by looking at the maturity of your sales

Coming out of COVID-19, many companies are looking for ways to make up lost ground or revenue, and often the approach is to hire a strong sales leader. When thinking about who the ideal candidate is, the knee jerk reaction is to find someone with a substantial Rolodex and/or a certain amount of industry experience. But that is where I want to pause. Before determining this, you first must ask yourself, “where is your company relative to sales maturity?” I find this is often overlooked and to find the best candidate to meet your needs, this is a key question to ask yourself. Knowing where you stand will help determine the type of experience that is required for success in the role and help you find the right candidate to fit with your organization.

Use the right tools

To start, I recommend that you use a sales audit tool to assess the maturity of your sales. Typically, they measure several sales functions which include:

  • Customer understanding – How well do you know your customer base? What is your value proposition to the ideal customer? This can range from having no understanding of product/market fit to having a well-defined product/market fit along with a tangible value proposition.
  • Technology – What technology do you have in place? Some organizations don’t even have a CRM system, whereas others may have bi-directional CRM and various operational/financial platforms with reporting and dashboards.
  • Tools – What formal support tools do you have? This measurement considers whether your sales collateral (e.g., proposals, brochures, case studies) is easily accessible in a central location and fully supports the key stages in your defined sales process.
  • Process – Do you have a sales process and, if so, what are the stages? This can range from no formal sales process (e.g., suspect, prospect, qualified, etc.) to a formal process with understood metrics of sales conversion and length of time at each stage.
  • Metrics – How do you measure and track success? Do you have well-defined metrics that are measured and reported? Some organizations have no metrics whereas others measure things such as win ratios, success rates in specific industries, verticals, and size of the company, etc.
  • Results – How well do your salespeople perform? You may find that your new sales reps rarely hit quota, or you may have many new reps hitting quota and having a win rate that is at or above the industry average.

When looking at this list one thing is clear, none measure Rolodex or years in the business. To help explain why we can turn to a typical scenario of a mid-market company (<1,000 people with 10 reps) that wants to hire a new Vice President of Sales.

A typical scenario

This organization has had a lot of success but wants to get to “the next level.” As they build their job description and map out a plan to identify the desired attributes, experience, and background of target candidates, they agree it should be someone that has led large teams from an enterprise-sized competitor. The focus of the search profile and job description is on:

  • Achieving revenue targets and wallet share
  • Working with the sales team to make/exceed quota
  • Attending conferences and tradeshows and being visible in the market

But here is the thing. They missed the critical first step of reflecting on their sales maturity. If the organization were to look at just one sales maturity function, Customer Understanding, they would find that they rated themselves on the low to medium end of the scale. They have a qualitative value proposition and an agnostic product, meaning they can sell to many verticals, but the challenge with that is someone coming from an enterprise firm has likely been fed some or all the Customer Understanding information through training, territory segmentation, and marketing.

Taking this a bit further, the difference between a qualitative value proposition versus quantitative is polarizing. People buy numbers…why? Because it’s easier to make a comparison. And taking a value proposition from – “we are outstanding and pride ourselves on quality and have the best people” to “we reduce customer downtime by X and have a failure rate of Y” is the next level. If you don’t believe me, ask yourself this – how many times have you looked at the number of Amazon stars a product has before you buy something, even if you don’t buy it off Amazon. See what I mean?

If the organization’s value proposition is sorely lacking, the individual they might want to consider is a failed or successful entrepreneur. Someone who has experience working long hours, grinding it out, experimenting, and building out Customer Understanding – including maturing a qualitative value proposition to a quantitative one, segmenting the market to understand the ideal customer (aka buyer persona’s), identifying the verticals that they should target, and drafting the necessary messaging to earn meetings and conversations to fill up the sales funnel.

Success starts with self-reflection

Sales and business development have changed more in the past 10 years than they have in the past 30, mainly due to technology. Gone are the days of walking/talking brochures and classifying someone as a hunter or a farmer – more on that in another article. As a result, you need to reflect inward before looking outward for your next sales leader, or you risk being disappointed and suffering from lost opportunity cost and turnover as a result.

Do you need to do a full-blown assessment of the maturity of your sales? No. Should you do a bit more self-reflection on how you get business and the tools and processes you have in place before you start looking for your next sales leader? Yes … yes, you should.  Once you’ve completed that step, you should use your detailed search profile along with candidate self-assessments and structured interview techniques to flesh out whether the candidate has the required background and skill-set to tackle the challenges at hand and mature the sales at the organization.


Download the PDF version of the blog here.


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