Operational Scalability: Jen Bergren On How To Set Up Systems, Procedures, And People To Prepare A Business To Scale

Create a culture of transparent communication. Share information across departments and levels of roles. Make information visible, in shared communication channels, accessible documentation, shared project management systems, and more, as opposed to a culture that defaults to private, unrecorded calls or private messages as the main form of communication. Give people access to information to understand business decisions, keep people informed of changes before they read about them in the news or on social media, and foster psychological safety so people feel comfortable asking questions to better understand all the changes that will happen as a company is scaling.

In today’s fast-paced business environment, scalability is not just a buzzword; it’s a necessity. Entrepreneurs often get trapped in the daily grind of running their businesses, neglecting to put in place the systems, procedures, and people needed for sustainable growth. Without this foundation, companies hit bottlenecks, suffer inefficiencies, and face the risk of stalling or failing. This series aims to delve deep into the intricacies of operational scalability. How do you set up a framework that can adapt to growing customer demands? What are the crucial procedures that can streamline business operations? How do you build a team that can take on increasing responsibilities while maintaining a high standard of performance?

In this interview series, we are talking to CEOs, Founders, Operations Managers Consultants, Academics, Tech leaders & HR professionals, who share lessons from their experience about “How To Set Up Systems, Procedures, And People To Prepare A Business To Scale”. As part of this series, we had the pleasure of interviewing Jen Bergren.

Jen Bergren creates courses and other educational content using human-centered operations topics to help people succeed in their careers, including a business process documentation cohort course and a RevOps bootcamp for HubSpot Academy. In her previous role as Head of Operations at Remotish, her work included creating plans, processes, and programs such as a knowledge management program (wiki), a comprehensive employee onboarding program, and a referral partner program that generated 50%+ of company revenue. She was also a professor for the HubSpot RevOps certification and works as an evaluator for marketing graduate courses for Western Governors University. Her book, What is RevOps, is scheduled to be published in late 2023.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Like many people, I fell into operations after having several other careers. My first career was as a graphic designer and art director, mostly for magazines, after completing an art & journalism degree. Photography piqued my interest while directing photoshoots for the design projects, which led me back to school to learn photography. My second career was as a photographer and entrepreneur of a photography art business. I enjoyed learning all about business. My favorite part of running that business was marketing, which inspired another career change a few years later. I completed an MBA in digital marketing to help my career move further and faster, as I was starting it later than many people. After graduating I began working at Chief Martech Officer (now called Remotish,), a technical HubSpot agency, beginning in a client-facing role on the fast track to management. While helping grow the company as one of the first employees, I discovered part of what I was doing throughout all my previous careers was actually something called ‘Operations,’ which was not just manufacturing supply chain management as my one operations MBA class would lead you to believe. Moving into an operations management role at Remotish allowed me to further focus on building and improving helpful people-centered programs and processes such as a knowledge management program, employee onboarding program, and referral partner program that earned up to 50% of revenue. About a year ago, I left that role to work for myself again. Now I’m creating educational content about operations topics to help more people learn these lessons faster and easier than I did, so no one has to start from scratch as I often did for many projects.

You can read a longer version of my career journey in this article.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I’m not sure which career to talk about as, ‘when I was first starting!’ I’m not great at thinking of funny examples, but I can share one big lesson learned from my previous business: don’t spend a year on your branding and your website before launching or before testing any products/services on actual customers. As a designer, this type of work was my comfort zone, making myself look and feel like a ‘professional’ business, but it was not the best use of time for learning how to be a profitable business. Getting real customer feedback about what you’re selling is more important than how the website looks, or having a memorable brand, when you’re in the first stages of business.

What do you think makes your company stand out? Can you share a story?

Right now my company stands out because there are very few companies offering operations educational resources such as courses. This is why I started the business. I didn’t want people to have to go through the same time-intensive research journeys, and all the trial and error I did, in order to invent processes and programs from scratch at my previous company. It’s 2023, no one should need to invent anything from scratch, everything has been done before by someone else! The information may not have been documented and shared very well in the past, which is why I couldn’t find answers online for many of the problems I was trying to solve in my previous role. I want to help shorten the learning curve by sharing information about operations and making solutions easier to find online and in communities.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

The main trait would be curiosity, the trait behind my passion for lifelong learning. I’m always wanting to learn more and know how things work. Though on paper, it may appear that my career and education journey is random and a result of changing my mind often, it was actually an evolution of wanting to learn more and dive deeper into a specific topic or skill I was practicing in my current role or business. This curiosity has served me well in an operations career, where generalists like me thrive, as we’re constantly learning about all aspects of the business and often working on vastly different types of projects at the same time. There is always more to learn!

Two other traits or abilities that have helped my career are creative problem-solving and a constant quest for clarity. As a result of my diverse career background, I can generate surprising solutions with an unconventional perspective to connect disparate ideas, see the big picture or long-term strategy, and then clearly explain the plan of detailed steps to make those ideas into reality. An example of this trait is the department roadmap process I created in my last role.

Seeking clarity is also related to curiosity, asking questions to understand concepts more clearly and focusing my communication efforts on being clear above all else, to help other people understand. The quest for clarity inspired my current focus on teaching people about documentation, because documentation clarifies processes, responsibilities, and more.

Leadership often entails making difficult decisions or hard choices between two apparently good paths. Can you share a story with us about a hard decision or choice you had to make as a leader?

I’m curious to understand how these challenges have shaped your leadership.

One hard decision I had to make as a leader was choosing between managing people, which was helping a small number of people directly and personally, or deciding to help people at a larger scale such as by creating people-focused programs across one company, or at an even greater scale by helping people across many companies learn about useful topics that aren’t often discussed. I enjoyed learning about being a good people manager and applying what I learned to manage my team, and there was fulfillment in directly helping people succeed in their careers. But as an introvert, focusing all my attention and efforts on the relationships and success of people I cared about was exhausting for me, compared to spending my time researching, creating, testing, and building. All those management learnings and experiences informed the people-focused programs I created as well as the human-centered operations topics I now educate people about. Though this decision means I may not achieve the C-level roles I had set as a goal when earning my MBA, I think this was a good decision to make better use of my skills, help more people, and not create a constant cycle of burnout for myself.

Thank you for all that. Let’s now turn to the main focus of our discussion about Operational Scalability. In order to make sure that we are all on the same page, let’s begin with a simple definition. What does Operational Scalability mean to you?

Similar to the purpose of creating my business, because no one should need to solve problems from scratch in 2023 and beyond, I would like to share an existing definition of scale.

Sam Jacobs, Founder and CEO of Pavilion, clearly defines scale as ‘profitable repeatability,’ during its Rising Executives education program.

You need to be able to predictably and consistently repeat what makes your company profitable. A strong operations foundation will make your processes successful, repeatable, less stressful on your team, and ready to serve the increased demand for your product or service.

Which types of business can most benefit from investing in Operational Scalability?

Businesses who want to achieve their growth goals in less time and with less stress. Even a one-person business can use operational scalability tactics to work fewer hours and have less stress about their business.

Why is it so important for a business to invest time, energy, and resources into Operational Scalability?

The time investment you put into operational scalability now will pay dividends exponentially in the future, if you set up your business operations to be sustainable and scalable instead of only performing one-time fixes and other reactive work that doesn’t prevent similar or related problems from occurring again in the future. One of the many reasons to invest resources into one aspect of operational scalability, documentation of your business processes, is to ensure that essential knowledge doesn’t leave the company when team members leave. Keeping this knowledge in your company reduces the time to train new people to operate productively and independently, reduces the strain on the existing team to answer the same questions repeatedly, and ensures you can predictably repeat past successes while avoiding making the same past mistakes.

In contrast, what happens to a business that does not invest time, energy, and resources into Operational Scalability?

Companies that don’t invest in operational scalability may never reach that point of inflection, that point of scale. At a certain point, simply hiring more people does not equal more productivity or more profits, if the systems aren’t in place to train people well, ramp them up fast, and give them the correct context to do their jobs without working off of faulty and incomplete data or repeating past mistakes. Your team needs to be able to consistently perform the same quality of work (or better), across the team, each time the process is performed, to allow for predictability and repeatability in your business.

Operational scalability allows your people to focus on the jobs they were hired for instead of spending their time building new projects on top of a shaky or non-existent foundation, constantly creating workarounds, and getting frustrated by the problems caused by the lack of business infrastructure. They will be fighting against tech debt from messy tools that don’t integrate or create a single source of truth for reporting, and fighting against documentation debt by solving mysteries all day and answering questions constantly instead of working on anything that will achieve the business goals. You can think of this as your people trying to dig themselves out of a hole, or maybe building a ladder in that hole to just to get up to performing baseline activities, but none of that activity is achieving growth above the baseline. This frustration leads to high employee turnover, and an inability to train new people in a efficient and effective way to not repeat the trial and error and mistakes of the previous person. This ends up being a never-ending cycle where you’re running in place but never getting anywhere until you invest in operational scalability. In short, you won’t be able to grow your business.

Can you please share a story from your experience about how a business grew dramatically when they worked on their Operational Scalability?

In my roles at Remotish, we had documented and refined our processes, and we worked on other aspects of operational scalability, from Day 1. Because of this foundational work, I was able to create a robust onboarding program in our third year of business, to enable us to double the company quickly from 10–20 people in 6 months when we forecasted an increase in client demand and revenue. Though scaling is about more than hiring people, as a service business, our people were our product . In order to serve more clients, we did need to add a certain number of new team members to keep up with client demand.

Those new team members said they felt supported since they had access to this documentation to know how everything worked. They didn’t have the burden of figuring it all out for themselves in their first month on the job. They didn’t have to wait for someone to be available to ask in real-time, which would be a bottleneck since we worked remotely and flex-time in multiple time zones.

We also would not have been able to attract as many top candidates when we were hiring quickly, if we did not offer a reduced work 30-hour workweek benefit that was only possible since our processes were documented. Documentation not only allowed people to complete their work more efficiently, getting 40 hours of work done in 30 hours of time, it also enabled our small team to cross-train and fill in for each other when co-workers were using their 10 hours a week of paid leave.

Expecting someone to remember how to do everything in their job, and also how to do someone else’s job, is not realistic. We’re humans, not machines. Set up operational scalability to create space for people to do their jobs more efficiently, effectively, and with less stress.

Here is the primary question of our discussion. Based on your experience and success, what are the “Five Most Important Things A Business Leader Should Do To Set Up Systems, Procedures, And People To Prepare A Business To Scale”?

My five tips are going to relate to focusing on your people first, which also relates to human-centered systems and procedures.

Create a culture of transparent communication. Share information across departments and levels of roles. Make information visible, in shared communication channels, accessible documentation, shared project management systems, and more, as opposed to a culture that defaults to private, unrecorded calls or private messages as the main form of communication. Give people access to information to understand business decisions, keep people informed of changes before they read about them in the news or on social media, and foster psychological safety so people feel comfortable asking questions to better understand all the changes that will happen as a company is scaling. Though it may feel vulnerable to share so much information with team members, it will be much harder to grow your business if you’re not retaining your team members, if you’re constantly re-training replacement team members instead of doing more impactful work for scaling. Change management will be easier if there is already a good culture of communication. As a company that celebrated remote asynchronous work enough to rename itself Remotish, we spent a lot of time focusing on creating and refining these shared communication processes, and teaching them to new team members.

Document your processes, and set up a system to keep your documentation updated and shared, spreading out these responsibilities to empower team members to own their work. Though documentation is a subset of the transparent communication culture in the above point, it needs to be emphasized further, with so many companies saying they don’t have the time to perform this critical step. You won’t be able to scale if the business processes are not documented. Enable your people with the information they need to perform processes consistently each time, with the same quality standard across the team, so you can achieve proven, predictable, and repeatable results. Otherwise, people will be spending their time trying to remember what they did last time, operating off of incorrect and incomplete information, or constantly answering and asking the same questions to other people. You won’t be able to improve your processes to make them scaleable if you can’t see and agree on how processes currently work or how they should work. You won’t be able to efficiently test any new steps of a process, or new processes, if you’re not documenting your experiments to know what you’ve tried before or what you’ve researched before. If you’re not able to understand the outcome of those past efforts and how to repeat successes and not repeat mistakes, you won’t be able to scale. There are so many reasons for documenting. I would say this is my #1 tip, but if you don’t have a transparent communication culture in place, it is very hard to make documentation habits sustainable and useful across the entire company.

Make sure you have clear career paths, and clearly defined roles and responsibilities, for each team member. Define what it takes for each person to get a promotion and make sure it is the same promotion criteria for the same level of role across the company. This includes defining the leadership roles, with leaders modeling the behavior they want to see from the people who would earn a promotion. As mentioned in tip #1, be transparent, make these job descriptions and promotion criteria accessible to everyone in order to understand each others’ responsibilities. Amidst the high stress and constant change while scaling, team members knowing there is a clearly defined path to be rewarded for their effort could be the difference between retaining or losing your top talent at this critical time. These job descriptions also help direct people to the right person when they have a question (a question not answered by documentation). Clear job descriptions also lead to better hiring decisions, which is important because one bad hire can cost your company a lot of time and money while preventing progress toward your goals.

This will likely be a lot of respondents’ #1 answer, though I think the above steps are more critical: Make sure your tech and data are integrated, streamlined, shared, and trustworthy so everyone can make accurate business decisions using forecasting, reporting, and more. This could fall under the ‘people’ category by enabling people with accurate information and useful tools. (Also — document how your systems work so it is easy for people to fix any problems and make improvements.) Making gut-feeling decisions is not a good strategy, especially as the company grows since it will be impossible for one person to track everything in the company in their head to make an informed decision. Many team members will be responsible for smaller and smaller parts of the business, compared to in a small business where people may be working cross-functionally in many roles at the same time so ‘gut’ decisions are more informed by the big picture. The role of tech usually gets the most focus when talking about operational scalability, party because it is a more tactical aspect to plan compared to the people side of the business, and partly since there are tech companies that want to sell their products by dominating the conversations about operations and scale.

If all the above tips sound like a lot of work…you’re right. So why not hire someone to help you put these plans into place? I suggest hiring an operations person or team to help you with the above work before you think about scaling, instead of the common practice of waiting until you’re ‘big enough’ to justify the ‘expense’ for this role. This investment should not be thought of as an expense. A good general ops person will take less time to set up, test, and iterate on these operational scalability foundations compared to hiring the same talented person or team after you attempt (and fail) to grow the business because your systems, processes, and people are a big mess that ops would have to investigate, untangle, and solve before anyone can make progress towards business growth goals. Invest in operations people first, before attempting to scale.

There is also a lot of work to do with your product or service offering, and your customer service/success processes to make sure you can serve more customers using fewer team members than the past ratio of team members to customers, while maintaining or improving customer satisfaction and referrals. That could be 5+ tips in itself so I’ll leave that topic for a customer-focused leader to discuss. They will have more relevant advice about that aspect of scaling.

[Here is the video for this — https://youtu.be/0SYvbqdsQhc?si=eDxHw98T53MHZOHJ ]

What are some common misconceptions businesses have about scaling? Can you please explain?

One common misconception is that scaling just means hiring more people to be a ‘bigger’ company. To further build on this, a misconception that simply hiring more salespeople will lead to an increase in revenue and therefore, profits, without any increasing investment in operations to create foundations for scale. The math does not work that way in real life.

How do you keep your team motivated during periods of rapid growth or change?

The transparent communication tip above will help keep the team informed of what’s happening now, what will happen next, and why it’s happening. You can increase motivation by decreasing uncertainty, showing a clear plan of where you are now, where you will be in the future, and what it will take to get there, including many reminders of the benefits to the company, teams, and individuals for completing this rapid growth or change. Breaking up the change into small goals can motivate people by having clear, manageable next steps that can successfully complete instead of overwhelming them and causing procrastination. Celebrate small wins during the change, even if it’s just with a gif party in Slack to celebrate a person or a team’s work. As a manager or leader, reach out and offer to help and support your team often. Don’t let people feel alone in the uncertainty of change. Don’t let your team feel like they have to figure everything out themselves in this new and unstable environment.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My favorite quote is, “Clear is kind,” from Brene Brown. I’ve used this quote a lot in my work, as my former co-workers know, to emphasize the importance of clear communication. It’s related to the importance of documentation — if the information is only in one person’s head, it is not clear to other people, which means they are not being kind and helping their team members understand the process and to not repeat the same mistakes or same research. The quote also relates to Kim Scott’s principles of radical candor which was an important book as I was learning about managing people. It explains that giving someone clear feedback is helpful and kind, and withholding feedback for improvement is unkind. I also use this quote for myself to try to simplify ideas and concepts to make them more clear. My first draft of writing anything is usually long and rambling, so this quote reminds me to take the time to reduce it to the essential messages will more clearly explain my meaning and be more useful to other people, respecting the readers’ time (being kind).

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would start a movement of documenting and knowledge sharing as common practices! You’ve worked hard to learn a lot of important and useful information, so don’t only keep it hidden in your brain and nowhere else! Document it and share it with other people in a way that lasts, not just in private phone calls and private messages that benefit 0–1 people. Share your knowledge at a greater scale. You don’t have to think of it as ‘building a brand’ or ‘thought leadership’ or anything intimidating. Simply share your knowledge to help other people. Especially if you’re in operations, we tend to be behind-the-scenes people focused on getting everything done and making everything work so well that no one notices the effort behind it, so our knowledge isn’t as commonly shared or easy to find online compared to ‘louder’ topics like sales and marketing.

How can our readers further follow your work online?

You can follow me on LinkedIn or through my website.

Thank you so much for sharing these important insights. We wish you continued success and good health!