Restructuring and Rejuvenating the Sales Team at Customer.io

I joined Customer.io in June of 2021 as the VP of Sales. Throughout my career, I’ve been lucky enough to work alongside and collaborate with excellent sales leaders who brought unique leadership styles and perspectives to their respective teams. Through this, I’ve learned that there’s no silver bullet when setting up the proper structure for your sales team—there are many effective strategies, and the right approach is situational.

In 2020 Customer.io saw record growth, over 70% year-over-year, after introducing its Premium offering to the market and establishing its first true sales team. Customer.io primarily relied on inbound leads but was in the process of growing an outbound sales team to help accelerate growth. The structure was there, and the goal for 2021 was to double down on a tremendous year and continue the massive year-over-year growth.

With a rapidly growing sales team, I saw opportunities to improve our sales process and make the team more efficient to maintain our year-over-year growth. 

Reasons for Restructuring

Setting the team up for continued, scalable success was the ultimate goal when I joined the company, and to do that, there were some immediate adjustments to be made. By working alongside several amazing colleagues, we set these primary goals:

  • Unify the Sales organization as one connected team.
  • Lay a foundation for career enhancement and upward mobility.
  • Enable a culture of prospecting and self-accountability.
  • Increase time spent on high-value tasks to improve productivity.

6 Changes We Made to the Sales Org in 2021

With those goals in mind, we made these immediate changes within my first three months leading the team. 

1. Combining Inbound and Outbound Sales Development

The Challenge: The addition of an Outbound team created two separate teams with different goals, leading to gaps in communication and collaboration.

The Solution: We combined inbound and outbound responsibilities into a single role, Sales Development Representative (SDR). By doing this, we were able to maximize our coverage for inbound prospects while having the team primarily focus on outbound prospecting. This also allowed us to level the playing field for all SDRs to expedite career progression for top performers.

2. Sales Pods

The Challenge: We had a significant separation between our SDR team and Account Executives (AEs), where it felt like they had different goals and disjointed targets.

The Solution: We wanted to drastically change the structure to get everyone out of that mindset and become a connected team. I introduced Sales Pods consisting of two AEs and three SDRs for each industry we serve. This fosters collaboration and allows the team to help each other better understand what drives those customers and what features help their companies be successful.

3. Prospecting-First Mentality 

The Challenge: The SDRs did all the outbound prospecting and fed the leads to the AEs. 

The Solution: To become a collaborative team using the Pod structure, we adopted a prospecting-first mentality. We arrange our Sales Pods by industry vertical (EdTech, FinTech, etc), which aid for repeatable prospecting and subject matter expertise! By having the entire team source their own outbound leads, everyone becomes accountable for their results, giving them direct control over their success. 

4. Focusing on High-Value Activity

The Challenge: Lack of cross-team collaboration led to many internal discussions siloed from the rest of the sales team without any resolutions. 

The Solution: In sales, it’s crucial to spend time on “high value” activities directly related to obtaining your quota. For example, sales reps should maximize time spent with clients directly, advance new business opportunities, and limit time spent in non-selling activities such as process discussions and internal meetings. When joining the team, one of my main objectives was to reduce the amount of time that reps were spending on operational tasks and pave the way for hitting quota across both the AE and SDR teams. To do this, we developed a Sales Operations team, improved collaboration with Marketing Operations, Billing, Customer Success, and other internal departments to clarify roles and responsibilities and create efficiencies every step of the way! 

5. Career Pathing

The Challenge: We were laser-focused on hitting quota that we didn’t have a defined and documented career path, leading to decreased trust and a lack of confidence in career advancement at Customer.io. 

The Solution: We first needed to find a way to continually hit the quota. The previous five changes helped us achieve that. Career progression wouldn’t come off as genuine until we could repeatedly attain quota. There’s a big difference between showing a set career path and just talking about one. We couldn’t talk about it without showing the team an actionable plan and career ladder they could easily understand. We’ve developed a sales career pathing plan for SDR to Sr. SDR or SDR Manager to AE to Sr. AE. Each role is clearly defined and eliminates any confusion around career advancement opportunities. 

6. Performance-Based Promotions

The Challenge: We grew a large SDR team but didn’t have any guidelines set around when they’d get promoted.

The Solution: The SDR team is the engine that powers the sales machine. When firing on all cylinders, opportunity creation is up, deals are closing, and life is good. Top-performing SDRs need not only to be celebrated but also allow for advancement within the team and company. Following the sales career pathing we set, SDRs are eligible for promotions based upon their individual quota attainment over a six-month rolling period. Since the SDR can either go down the AE path or SDR Manager path (among other options), we try to have these conversations early on and make sure we’re setting them up for success and are aligned with their personal goals and aspirations. 

These six changes have allowed our Sales department to overcome immediate challenges and create a sustainable foundation for growth as we continue to scale our team and bring in more customers.

If I can say one thing with certainty, change is constant for a growing sales organization. We’ll continue to iron out our process, tighten up areas that need improvement, and optimize the buying experience for our customers as we enter 2022 and beyond.  

“If everyone is moving forward together, then success takes care of itself.” – Henry Ford

Chris Parker

Chris joined Customer.io as the VP of Sales in June 2021. He lives north of Boston with his wife, two children, and dog.

Before Customer.io, Chris spent two years in Sales Leadership at Zaius, an Activated Customer Data Platform (CDP), recently acquired by Optimizely. Prior to Zaius, he spent nearly a decade at ownerIQ, a Second Party Data Marketplace for Retailers & Manufacturers. 

Connect with Chris on LinkedIn

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