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The Challenges of Scaling a Sales Organization

The Challenges of Scaling a Sales Organization

Scott started in various sales roles with Chili Piper and built out much of the sales operations infrastructure. His current role is a mix of sales ops, customer service ops, marketing ops. He’s also involved in some aspects of financial operations that take place after deals are closed.

In the past year, Chili Piper has raised series B funding, and their headcount has grown from around 50 employees to 150 employees. Adding an extra 100 people has brought new challenges in hiring, training, and onboarding new salespeople and operations staff.

Sales Enablement Readiness for Sales Org Growth

When Scott knew they would hire many sales reps, they had to make sure they had all the enablement material ready to replicate and train the reps effectively. Their goal was to decrease their onboarding ramp period. Toward that end, they had all information for different departments documented in Google Drive. Each department head owns the material and how those first 30 and 60 days are planned out for each role.

Three core things were the focus of their onboarding: tools training, internal sales process training specifically for that role, and skill set training related to that role. So, for example, an SDR’s training would be around the skillset and tools used to get the prospect interested in booking a meeting or trying to get them to close the deal.

Tools also enabled the training. They implemented Gong to help AEs and account managers understand the flow of conversation with different customers and use cases. And then for SDRs, there’s a mix of various tools. Eventually, Scott evaluated LMS platforms and ended up using WorkRamp.

Scott shares that when Chili Piper’s sales team was small, they could hop on Zoom or chat with people on Slack, and everybody knew what was going on. But when you get bigger and have so many new people coming on board, you need documentation of your sales processes. WorkRamp enabled them to do that.

Common Issues in Scaling Sales Team Growth

During onboarding, common questions would arise from the sales reps, such as how to close on an opportunity, handoff information over to the CS team, and expense items for trips. They had to document those questions and answers for each department, and each department head owned their specific niche information. Now they use Guru for internal knowledge management, and they’ve implemented it company-wide. The tagging and search features and integration with Slack and Gmail make it easy for reps to use day-to-day.

Once Scott established the training and onboarding environment, they established the departmental headcounts by working backward from company revenue goals. Chili Piper has a financial model they use. Each department has its reporting and headcount capacity metrics, and planning for the following year rolls up into this model. It’s all based on the departments’ specific metrics. For a closing role, it’s revenue-based. For marketing or sales development, they look at pipeline.

The components of their revenue number and financial model include how many meetings on average a rep should maintain to have this much pipeline. They also look at conversion rates and determine how much sales reps should bring into the business. Then there are more granular metrics such as how many reps they should have on the sales team to hit their new business number. They also look at how many account managers they’re going to need and how many accounts each one can realistically manage with their capacity and the number of meetings and miscellaneous tasks involved.

Planning for the Year Yet Staying Agile

We asked Scott how he plans a year in advance yet stays agile enough given the fact that things might change while still planning so far ahead? Is there a break-even point? Is there a margin of flexibility there? How does that work in practical terms?

Scott shares that there’s not just one model in place. The agile piece is that they have different models with different scenarios for curveballs that can occur, like COVID. They have plans for the worst-case scenario and best-case scenario.

Sales Organization Structure

Compensation planning and commission structuring for the teams was one of Scott’s initiatives while scaling the sales function at Chili Piper. Before series A and series B, they had some infrastructure for their SDR, AE, CSM, and account management team. As part of the hiring process, they wanted to ensure they correctly allocated managers to reps. Once they nailed that ratio of reps to sales leaders, they developed more compensation plans for management and individual contributors.

As salespeople get promoted or go from an SDR to an AE, they have plans for each of those progressions. They have it documented in terms of the payout rules and the infrastructure to support it inside of Salesforce. They used a lot of sales spreadsheets until they had it working smoothly. Then they automated and replicated it in a platform.

Processes and Tools for Sales Team Compensation

There are a few ways sales professionals at Chili Piper can engage prospects to get compensated, but it’s fairly straightforward. AEs just close won deals, and then there are accelerators or decelerators based on attainment. Similarly, with account management, SDRs are paid on qualified ops, and then they are incentivized for close won deals with their source. And then, the CSM team is primarily incentivized on that logo retention and gross star logo retention.

Once Scott’s team built this out, they evaluated different commission software platforms. Ultimately, they decided on Spiff for the sales team’s platform. Spiff does a super clean job of outlining how all the payout rules work and how the plans and quota tables will look in their platform. And then, it was Scott’s responsibility to build out the infrastructure, calculate commissions, and manage it for the reps’ payout every month.

Since they have the infrastructure in place and have implemented Spiff, the process has been more hand-off. As a result, Spiff has reduced the time involved and the errors in their payouts. They have a monthly meeting with sales managers, the AE manager, and the SDR manager. They look at new hires and people transitioning out of the team to different roles or departments, input the dates and add new people, and Spiff does all the calculations.

Invest in the Operations Department

Scaling your sales organization means the operations department is going to have many tasks on its plate. You’ll need a system for establishing important and urgent priorities. This system helps manage expectations with other people internally because they will not necessarily know how long it might take to build out some of this.

You’ll also need to champion for headcount in the sales operations department because once you understand the backend builds and the user experience that you can bring the sales team, there’s a huge uplift.

Workflow and user experience are essential. If you have the right people in ops who know how to make it look and work smoothly for the sales reps, you can remove more roadblocks faster and develop a repeatable sales process, which will help you plan for growth and onboard new reps. Documentation might not be the most enjoyable part of the job, but it’s probably one of the more critical pieces.

Scott also advises making sure you’re having fun and maintaining your mental health so you don’t get burned out. There will be many tasks on your plate in ops, but make sure you’ve got the right mindset about it.

Periodically take a step back and see what you can get rid of, automate, or delegate to others. This will help you focus on the higher-impact priorities.

Follow Scott on LinkedIn