5 reasons why growing companies struggle to build Engineering teams

Brian Zotter is the Co-founder and CTO of Cacheflow. He talks about the challenges of building engineering teams at hyper-growth startups without the right tools.
Brian Zotter
Co-founder at Cacheflow
min read
January 9, 2022

About Brian

Brian Zotter has been in software engineering for over 20 years. He’s built and scaled large engineering teams at Salesforce and Medium, and he’s now the Co-founder and CTO of Cacheflow, a “Buy Now, Pay Later” solution for B2B SaaS. 

Throughout his career, he’s run into the same challenges over and over when trying to grow his teams.

Even as he built an engineering team of 120 in roughly four years at Medium, Brian was managing a huge portion of the headcount planning, hiring, and onboarding for all new employees. It wasn’t the most efficient way to scale an engineering team at a hyper-growth startup. 

In this blog post, we share Brian’s top five reasons why it’s so difficult to build and scale an engineering team, even when the company is anxious to grow.

Brian's Top 5 Reasons It's Difficult to Scale Engineering Teams

1. There are a dozen spreadsheets to keep track of - literally.

Most engineering leaders today – if they’re highly organized – manage all their employee information in spreadsheets. This includes level, skills, domain experience, promotions, and compensation, as well as details of open headcount and backfills. 

Meanwhile, finance plans the budgets in their own separate spreadsheets. Hiring managers and recruiters use different spreadsheets to track applicants and hiring milestones. And as the VP, Brian had an “aggregated spreadsheet,” which collated top-level information, total budgets, the number of roles, individual job levels, and more from each of his teams. 

Clearly, there are a lot of spreadsheets in the headcount planning process. Engineering leaders often spend too much time maintaining and updating multiple spreadsheets — across hiring, capacity building, and organizational planning — that don’t connect.

 “At one point, we dealt with 15 different spreadsheets for each hiring manager that constantly needed to be in sync,” Brian recalls. 

This chaos slows down planning, hiring, and onboarding, and it creates disconnects across key stakeholders like finance and talent acquisition.

2. Not enough time is spent on strategic organizational planning.

Let’s say you know you need to hire twenty people. How do you go about it? Will all twenty be net-new? Will you promote someone and backfill their position? How do you decide which manager gets which headcount? How do you account for span-of-control? For diversity? 

Organizational planning is not just about tracking progress, but also visualizing the present and the future. Engineering leaders need more than just a spreadsheet to gain a clear 360-degree view and drive strategic conversations. 

In Brian’s experience, these strategic conversations aren’t one-time activities. They happen at least every quarter, even once a month, at growth companies like Medium and Salesforce.

Yet, when leaders are bouncing from spreadsheet to spreadsheet, from one platform to another, and trying to manage through messy headcount processes, it’s really difficult to add meaningful value to strategic conversations at the highest level.

Without strong org planning, growth startups struggle to build strong engineering teams.  

3. Little fires pop up everywhere.

It is vital to be transparent and open about changes at startups. Yet, untimely and out-of-context information can do more harm than good. This can easily happen when all headcount planning is managed in spreadsheets; access control gets tricky. 

For example, Brian and his team would utilize the various spreadsheets to run scenarios with different team structures. 

“Once, a manager viewed a spreadsheet while leadership was deciding whether we should move their team to another group. They saw this potential change and understandably got upset. It cost us a lot of time downstream explaining the context and thought process behind the scenario,” he says. 

This is just one example of the types of “fires” that engineering leaders are managing through on a regular basis throughout the growth process.

Without proper access controls, engineering leaders can find themselves giving lengthy explanations about their strategy and approach, rather than focusing on growing the team and achieving goals. 

Not to mention, the matter of privacy and confidentiality becomes much thornier when the planning process is not as tight as it should be.  

4. It is challenging for Finance to keep track of evolving decisions. 

Brian's biggest challenge was that finance provided a top-down view of the annual budget that didn’t accurately reflect reality in a world where things were changing daily. 

“We need to know how much money we're spending, but it shouldn't dictate the hiring plan,” suggests Brian. “For example, I might be able to take the same sum of money we set aside for two Level 1 engineers and go get one Level 4 engineer for a team that became a higher priority. But my budget needs to be as agile as my plan,” he says. 

This isn’t always the case. The challenge is magnified when there’s no standardized way for hiring managers to share updates and seek approvals for changes in the plan. 

“Some managers would send me the updates on Slack, others would email, and some would update a spreadsheet somewhere. It fell on me, as the VP, to update the finance team manually each time a change was made.” 

Without timely communication, finance is out of the loop and wastes a lot of time keeping everyone aligned.

5. There’s no single collaboration tool with accurate data for headcount planning. 

Today's biggest challenge to the headcount planning process is the lack of a  unified tool that provides up-to-date data from different sources and enables appropriate access to all people involved. 

Growth companies invest in people and platforms to help them recruit talent, track applicants, manage benefits, budget properly, and house employee data. But all of these systems are siloed, as are the people who work in each of them. 

“I wish there was one tool where I, or anyone I’m dependent on, could go and see the state of the org, so that engineering, recruitment, HR, and finance were all in sync about headcount planning,” says Brian. 

In this post-COVID, remote-first world, such a tool might be more valuable than ever before.

How do you drive strategic conversations with spreadsheets? You can’t.

How much transparency is too much transparency?

Finance is left to pick up the pieces.

The alternative? A single tool with accurate data.

How to reduce the burden of headcount planning 

Brian explains, “At Cacheflow, as an early-stage company, we're focused on values. So we're being very intentional from the beginning about how we plan the org, and how we screen, test, and hire.” 

To mitigate the many challenges of headcount planning on engineering leaders, growing companies need:

  • A single source of truth provides up-to-date information to make people-related decisions in real-time. 
  • A place for leaders to collaborate without concern of inadvertently frustrating colleagues. 
  • Automated notifications and updates to keep teams in sync.
  • Ability to forecast and identify non-performing team members to design the right interventions at the right time.
  • Ability to to provide complete visibility into critical systems like ATS and budget planning software.

Sign up below to see how TeamOhana has become the unified people platform that helps growing companies mitigate all the issues Brian laid out above.

You can watch our full conversation with Brian here.

To learn more about TeamOhana and strategic headcount management, contact us.

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