Scaling tips: Hiring a sales team

When you write a brief to hire a senior executive in any function there is the question of how you make the hiring process as actionable and insightful as possible. It should test whether the individual in front of you is able to do the role and give your company a glimpse into how that person will perform once they’ve joined. It’s equally important to give the candidate as much exposure to what your corporate mission is and how you and your organization think and behave.

Designing the correct hiring process when recruiting a Chief Revenue Officer or Head of Sales is especially important given the minimum expectation that anyone interviewing for this kind of role is going to be very adept at selling themselves. You need to drive the discussion and develop a set of questions that really assess capability and style that goes beyond storytelling. Unlike when you hire other senior executives in for example, engineering, where you can assess practical skills immediately, it is often 6-9 months into a role before you’ve fully validated how the CRO will perform and behave. 

It’s also clearly imperative that any process accurately reflects your company culture as the candidate is not the only one being assessed!

When first thinking about hiring a CRO or Head of Sales it’s important to gain clarity on the mission and the purpose of the role since, although it may seem surprising, the organisation can often have divergent views on why the role exists. It doesn’t need to be sophisticated, the simpler and more specific the better e.g.

- To grow revenue through direct contact with customers

- To design and execute an effective go to market strategy to enable the organisation to achieve its goals

- To be a figurehead in the organisation both internally and externally

- To build sales channels 

- To seek new industry verticals

Once you are clear on the mission and purpose of the role, aim to outline 3-5 outcomes for the hire and prioritise them in collaboration with the hiring panel e.g.

- To achieve 100% y.o.y. growth in revenue

- To increase EBITDA margins from X% to Y% over 3 years

- To upgrade the sales function through hiring leaders in all key markets in year 1

- Increase geographic spread of revenue

- Increase customer satisfaction and retention by x

Following agreement with the Board and hiring team on the objectives and mission, you need to prioritise the skills, experience and background that your company requires.

Whilst not exhaustive, below are some of the questions I would start with:

- Is it important that the candidate has done it before or is it important that they have experience at real scale and complexity?

- Is domain/ market experience important?

- Is experience of failure a benefit?

- Is it important that they’ve done the role before or have ‘high potential’ and if the latter how do you test for it? 

- Is it important that they are willing to roll their sleeves up and lead from the front or are you looking for a strategic individual?

- Are you looking for someone to execute an existing strategy or someone to write the strategy and then execute it? 

- How do you assess cultural fit? Are you clear on what your culture is as a business and how does that translate to what sort of sales function you want to drive? 

- Who needs to be involved as part of the process from your organisation both from an assessment perspective and who is going to ‘sell’ your organisation to candidates?

These should act as a starting point and help you begin to structure the process and the type of individual you’re looking for. Then you can decide how you’ll assess any individual against the brief.

The below framework is one I’ve found to be incredibly helpful when interviewing candidates and while it’s not exhaustive, it provides a detailed structure to help you finalise what’s important, how to test around the key areas and who will be involved.

First design the desired characteristics:

Example Desired Characteristics

- Unquestionable integrity

- Highly intelligent

- High energy

- Demonstrable leadership skills and understands the difference between leadership and management

- Focused with high attention to detail

- Able to articulate failure and how they overcame it

- Cultural alignment and ability to become ambassador for the company

- Ability to design and execute effective go to market strategies

- Experience of building and leading international teams

- Experience and understanding of leading within a VC backed company.

Then confirm the desired experience:

- Desired Experience

- Sales Representative > Front Line Sales Manager > Strategic Sales Leadership

- Been part of or lead an organisation from scale-up ($5m in revenue) to $30 million in annual revenue (adjust as needed)

- Relevant industry or adjacent industry

And confirm who will be part of the hiring process:

- Hiring Team



- HR Director

- Board Members

- Members of the Sales Team (typically only involve in later rounds)

Finally build the interview questions that will enable you to test and qualify the above.