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  • Writer's pictureMichael Venman

Your Path to Smarter Business System Project Management from Startups to 500MM in ARR

Updated: Jul 31, 2023

Bad project management is a killer. Just look at Boston's Big Dig initiative from 1982 - 2009. (5 points for the oddly specific reference...)

I don't need to get into the importance of good project management and communication, but the needs of a company will vary incredibly depending on the size and the state of the business you are serving. Smaller companies won't have the interest or the focus to iterate on what you're learning every day and larger companies require predictable processes (and invest in them) as trust drivers with the team internally.

I recently began working with a company and had the opportunity to design it from scratch. As it's in the larger band of firms that I can speak to, it made me want to explore what lessons were most impactful and offer some helpful advice from each experience. My experience is from a Business Systems/RevOps leader perspective, so that's where I'll focus.

You're crawling and it's a struggle

Over the past 10 years, it's been clear that Operations is coming in earlier and earlier to scaling companies, which is a good thing. Nothing worse than showing up as the first Revenue Operations or Business Systems person as the 100th employee. In those cases nothing is documented and often you need to break poorly built and unstable implementations and then fix them. That means the first impression you have to the larger team is telling them they are going to lose functionality... very bad.

So, I'm gonna start instead on the preferred clean instance where nothing is built. The good news is that you get to build it all from scratch! Usually these companies are in the <$5 Million ARR range.

  • Everything is urgent because the business is still figuring out how it should build, sell, bill, and support.

  • Documentation isn't important because the Operations team is small.

  • You are the systems expert, and there aren't too many cross approvals needed for new implementations. That means that your boss has no clue what you do, and will only pay attention to you if it breaks or the data is wrong.

  • The cost of a down system or errors in production is smaller, so often for simplicity's sake you'll just build directly in production.

  • You're constantly getting dragged in different directions and are plagued with sales reps saying "Hey [Name], you gotta sec?" every 12 seconds.

  • You'll fall into one of two situations, either you'll have tons of budget with too many systems to support or the be bootstrapped where you can't afford necessary systems and need to get creative... For me it's better to bootstrap.

  • You'll focus on Salesforce Dashboards, custom Data Analysis, and building new integrations for telephony/cadencing, data buying, and basic metrics.

Sounds like fun right?! Honestly, one of my favorite times of my life. The things you don't have all relate to structure, which can be your best friend or worst enemy. During this time the most important thing is to grow revenue as fast as possible. Don't worry about documentation or proving your worth or justifying your time - grow revenue and you'll be fine!

Mr. or Ms. Process

Whew! Made it past the baby company struggle, or have just joined, and are now at stage where you need to organize around creating rules and procedure. You might still be a team of one (you rockstar you) or there is a team now that needs to function together to support the business, it's become imperative that you know who is doing what and when. I've usually seen these patterns up to about $50 MM in ARR.

  • The business is relatively stable and the day-to-day fires have slowed down.

  • The company has enough integrations and systems that no one person can really be an expert in all of it, so there is probably a team or 3rd party Consulting firm helping you out.

  • Coordination around time consuming efforts needs to be discussed if not receive sign off from another leader.

  • You have a case system where users can create tickets (duplicates in the system, errors they are receiving etc...) and need to triage issues daily.

  • Changes must happen in the Sandbox before you make them in production, because the cost of an outage is now noticed in lost revenue.

  • There is still "Hey [Name], you gotta sec?" but now it is every 8 seconds.

  • You have a budget now and can start to play offense with what you choose to build and implement.

  • If you are a manager, you'll have to learn to manage experts who know more about their field than you as your team grows.

  • You'll focus on developing repeatable processes by installing new platforms, managing internal cases, and start working on last 5% problems getting every last drop of juice out of the orange.

For those Sales Nerds out there like me, this can be exhilarating, right??? By focusing on the process you'll understand what your team needs to support the business and grow in the right direction. Using cases as a mechanism to identify and separate the work you do will be a huge win, especially as you start to establish Customer Support KPI's to your internal work.

Big Ship Problems

And boom - just like that, we're living at the TOP baby... (imagine "I'm on a Boat" playing off out of a gamification platform dashboard.on a busy sales floor)

Now you've got some big time puzzles to solve, investor pressure, and the initiatives that you implement are affecting top line revenue directly. Their success, or more notably their failure, makes big waves and is very public. Sales people open many cases each day, each immensely important to every individual that is stuck without them. You need to ensure you are staffed in the right areas for inbound tickets and you run both a Customer Support organization as well as a Product Development Team. This is the space in which I've done most of my work and has been true in my experience for up to organizations at $500MM in ARR.

  • Organization and planning is a key responsibility as you undoubtedly have 3 competing masters - Bugs and Critical Fixes, Planned Enhancements, and large organizational projects.

  • Your Bugs and Critical Fixes now have SLA's and CSAT surveys are not out of the question. Correct staffing and fluid planning are essential.

  • Internal sprints and deliverables as well as communication to the larger group becomes very important. You're now running a development team.

  • "Hey [Name], you gotta sec? My computer isn't working... can you help?" has been blocked off and everything goes through a Case.

  • Product Led Growth is almost certainly a part of your strategy.

  • Large projects such as new ERP/Marketing platforms or company acquisitions and mergers are happening concurrently all the time.

  • Your focus is how to staff concurrent priorities and will touch every part of the business from Lead to Cash to Delivery.

So what's your advice...?

I wrote out advice for each size of business, but it really came down to be very simple. Build a way to manage workload and plan with visibility to your external team. To do this, I've always used Salesforce's easy to customize platform to build the tool I'd like to use, I'd suggest you do the same.

  • If you're at a small firm, start by creating your own ticketing process using standard Cases.

  • If you're at a medium firm, mandate that usage and don't take "No" for an answer.

  • If you're at a large firm, create an Enhancements Object where you can track Acceptance Criteria, Solution Designs, and Test Cases to manage day to day tasks against future planned work.

  • If you're at an ENTERPRISE firm (over $500MM) I have no clue... so let me know if you do so I can direct people your way.

The most important factors to consider include the ability to group incoming work, assign responsibility, track the status and assign size (or time or points) to that work. In my experience, larger organizations need more structure, but as you transition from one size company to another, your ability to manage, demonstrate, and communicate your workload will become imperative.

Finally, no matter what you build or if you use an OOTB tool like Asana, it works if you work it. You are the first line of defense, and all the work you do should be entered. Make the expectation with your team that they create these cases, that you define what high priority "really" means, and that you have some way to horse trade. Communicate back to the business when a work item is complete and allow them to feel the wins you're producing!


If you do the above, and aren't successful, it's more of a people management issue. Either way, I'd love to talk to you about it. At The Sales Nerd, I work with companies to implement these types of changes in their Business Systems teams and have implemented over 50 companies to improve their GTM systems in the Salesforce extended ecosystem. Please reach out if you think we'd have fun talking or you have a project you think I can help with!


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