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Sales Leadership Advisory

I spent twenty-seven years in sales at Cisco, building and leading sales teams and finishing as an EMEA vice president. This advisory work applies that experience to three problems that growing sales organisations face.

Scaling to a leadership structure

A growing sales team needs managers before it needs more sellers. This takes a flat team to a layered one without losing momentum while it changes.

Who it is for. Founders who need to scale their sales organisation or companies who have seen rapid growth but lack the experience to expand effectively.

What is included

  • Review. Conversations with the leader and a sample of the team, and a look at how the team sells, who it reports to, and where it is straining.
  • Design. When to add a management layer, how many people each manager leads, what each role is responsible for, and which processes the bigger team needs and which to leave out.
  • Choosing managers. What to look for, whether to promote or hire, and how to tell a strong seller from a strong manager. Assistance with the interview process.
  • Developing the new managers. Four weekly sessions for the new first-line managers, covering one-to-ones, pipeline reviews, coaching and running a team meeting. I also sit in on the managers’ internal meetings with their teams, such as one-to-ones, pipeline reviews and team meetings, and give feedback afterwards. If there is a need to accelerate the training and learning, local on-site visits can be arranged.
  • Support. Monthly check-ins with the leader for the first months after the change.

Materials you keep

  • The structure chart and role descriptions.
  • Criteria for choosing managers.
  • The team’s meeting rhythm: weekly, monthly and quarterly.

The result. A structure you can grow into, managers chosen and trained for the job, and a team that keeps selling while it changes.

Time to complete. Approximately two months.

Forecasting with integrity

A forecast is only as good as the honesty behind it. This fixes both the process and the behaviour that distorts it.

What this is not. This is not sales training, and I do not teach a sales methodology. The work sits alongside whatever method the team already uses. It covers how leaders run the forecast, how they question it, and how they respond to what it tells them.

Who it is for. Sales leaders and their managers who need a forecast the business can plan on.

What is included

  • Review. How the forecast is built today, and how the last few quarters’ calls compared with what actually closed.
  • Definitions. Agreeing exactly what commit, upside and pipeline mean, in writing, so everyone uses the same rules.
  • Cadence. The weekly forecast rhythm, the pipeline review agenda and the questions managers ask to test each deal.
  • Joint session. Reps and managers together, calling real deals against the agreed definitions until their judgements line up.
  • Leader behaviour. One-to-one work with the senior leader on how they react to bad news, because that decides whether managers report what is really happening; also why people sandbag or over-promise, and how to spot it.
  • Forecast tracking. I set up a tracker that shows each week how the forecast is moving. It pulls the data automatically from a CRM with an API, such as Salesforce or HubSpot, or reads an Excel workbook the team updates, for smaller companies still scaling. Each week it shows what was called as commit against what actually closed, by person and by manager; deals whose close date keeps moving; deals that jump or slip stages; and deals that have sat too long without progress. Leaders use it to ask better questions in the forecast meeting. It supports their judgement rather than replacing it.
  • Live support. Sitting in on the team’s internal forecast calls across one quarter and giving feedback afterwards.

Materials you keep

  • Written forecast definitions.
  • The pipeline review agenda and inspection questions.
  • The forecast tracker, which keeps a record of every quarter’s forecast against what actually closed.

The result. A forecast process the team follows, and leaders who report the truth early.

Time to complete. Three months, over a whole quarter.

Optional extra: targets and incentives

This is for leaders setting the next year’s targets and incentive plan.

  • Review. Last year’s targets, results by person, and how the current plan pays out.
  • Setting targets. Choosing the method (from the top down, from the bottom up, from history or from capacity), setting realistic and stretch levels, and deciding whether the business can afford stretch this year.
  • Pay design. The split between base and commission; thresholds, accelerators and caps; how often it pays; and closing the gaps that let people game the plan, such as timing deals.
  • Managers. Presenting targets, explaining why they are fair, reviewing progress during the year, and running the conversation when someone misses.

Materials you keep. The target-setting method, written down for next year; a one-page plan summary for the team; and a talking guide for managers.

Leading leaders

Leading leaders is a different job from leading sellers. This is for the leader whose team is made up of managers, whatever their title, because titles mean different things in different companies.

What is included

  • The shift from managing sellers to developing managers: what to stop doing, what to start, and letting go of the deal.
  • Running a leadership team: delegation, accountability, one-to-ones with managers, and developing their coaching.
  • The operating rhythm: which meetings the leader runs, which they attend, and which they drop.
  • Composure and judgement under pressure, using my method.
  • Applying each topic to a real issue the leader is facing at the time.

Two versions

  • One-to-one. Fortnightly sessions over three months, with a minimum of six meetings per leader.
  • Leadership team. One offsite day on the principles, with working sessions on each topic, brainstorming sessions so the team contributes to how decisions are made, to the training and to the final outcome, and practice on difficult conversations. It is followed by one-to-ones that help each leader make the transition, a meeting about every two weeks over three months.

Materials you keep

  • A written plan for the leader’s role and team rhythm.
  • Notes from every session.

The result. A leader who builds managers, holds them to account, and stays composed when it matters.

Time to complete. Three months.

Times to complete are approximate. How closely an engagement keeps to its period depends on my availability and the client’s.

If you would like to talk

Write to me. I take a small number of clients, and the first conversation costs nothing and commits you to nothing. I will tell you honestly whether I can help you.

Contact me →

Or write to me at richard@gain-intelligence.com