Teamwork Makes the Dream Work Part 4: Reorgs & Team Structure

Holly Firestone
13 min readOct 19, 2020
Photo by Hannah Busing on Unsplash

This is Part Four of a four part series:

When I look back at my close to five years at Salesforce (4 years and 8 months to be exact), I’m incredibly proud of the impact my work and leadership had on our community and our company. It’s easy to look back and focus on all of the things I wanted to do- but didn’t, all of the things I did wrong, or all of the things I would change if I went back in time. I am working so incredibly hard to use those as lessons learned, but to also remember the things I’m proud of — and not be afraid to say that I am proud of them. It’s OK to be proud of work you’ve done! (I’m mostly saying this now to remind myself, but I’m sure many of you need to hear it as well).

There are two very big things that come to mind when I think of what I’m most proud of. First, is the Salesforce User Group Program. I made a strategic decision very early on that we needed to shift our focus and resources to that program. That decision and the execution of my vision for that program led to exceptional results, including making the community’s impact very visible to internal teams and leadership. The reason I mention being so proud of the User Group Program is because sharing the scope and impact of that program gives you an idea of how important I consider the second thing I’m most proud of — the work I did around my team. How I hired my team, how I managed my team, how my team viewed my leadership, and most especially, how I ultimately structured the team. So to conclude my Teamwork Makes the Dream Work series, I want to share the story of a reorg that led to an improved and impactful team structure.

Your Decisions Will Have A Huge Impact On Your Team’s Lives– No Pressure! 😬

Nobody likes change. It’s uncomfortable and the unknown can be really scary. However, change is inevitable and it’s required if you want to evolve and grow. As your company’s goals change, your community goals will as well. There are going to be basic goals around the health of your community that will be a constant. However, you have to always be thinking about how your community strategy is driving value for the business and how it ties back to your company’s goals as a whole. Because of this, your needs as a team will inevitably change.

The trickiest part about reorgs and restructuring a team is that this isn’t just changing the direction of a program or shifting budget around. This directly affects people — their careers, their livelihoods, their future. When it comes to making these kinds of changes, it can’t be taken lightly. It’s a huge responsibility. That alongside the importance of making sure your decision also benefits the company and the rest of the team makes it some of the hardest work you have to do as a leader. The structure of my team and the larger Community team had to change and evolve multiple times based on varying needs. I’m going to tell you all about one of those very special team structure evolutions.

There were two pretty impactful reorgs, and they happened just a couple months apart. So we made some changes in the first one, and then things quickly changed again. However, we did implement one improvement in that first reorg that I want to share.

Silos Create Solos, And That’s No Good 👎🏽

The community managers on my team, and actually across the larger community team as well, were focused on specific programs — two managing User Groups, one managing the MVP program, and one managing the online community. When we had our community managers focused on one program each, we were all in silos. I found three specific problems with this setup:

  1. Internal strategy- We often met with other internal teams to talk about community and how they can work with our team to get more involved. Besides me (and my manager of course), there wasn’t anyone on my team that could talk to other internal teams in depth about all of our community programs and how they could leverage them. I had to attend all of those meetings because I was the only one with a view across all of the programs. This sucked up my productivity and also hindered the rest of the team’s opportunities to build internal connections.
  2. Community experience- The audiences across the community programs had tons of overlap. For example, there wouldn’t be an MVP that wasn’t also a part of the online community. So when a community member reached out, they might need some type of support across a couple programs. They wouldn’t submit separate tickets/emails. They would write one — so what were we going to do? Pass them from one person to the next to help them with everything they needed? That would be ridiculous, but the current way was also causing confusion for our team.
  3. Career Growth- The team wasn’t being set up for success in their careers. Using the example of having two User Group Community Managers, it was hard for either of them to have ownership in their roles. There also isn’t really a specific growth plan for someone that’s a User Group Community Manager. What next? Senior User Group Community Manager? Director of User Groups? It’s not that you can’t be successful in those types of roles, but for where they were in their careers, and for where our community was in its maturity, it didn’t make sense to focus them that way. It also didn’t set them up for success both in their careers at Salesforce and their careers as community professionals when they left Salesforce. Strong knowledge across all of the community programs would only help them.

So in the first reorg, I took my two User Group community managers and made them community managers across all of the programs instead of program specific. I was also promoted to the leader across all of the programs. This meant I was running the online community in addition to the programs I was already running, the MVP Program and User Group Program. All community questions/support/requests came through a centralized support queue, which was great, but things still weren’t perfect. For our community managers, the ownership issue was somewhat worse (IMO), and career growth was still missing. I didn’t want things to be so narrowly focused on programs, but this caused things to be way too broad. It didn’t last long though, because just a couple months later, we had to think about another team restructure.

Red Rover, Red Rover, Send The Community Team On Over 🏃🏾🏃🏼‍♀️

The entire Salesforce Community Team was plucked out of our team and moved onto another team at Salesforce. Through this reorg, we picked up the Developer Community and programs and the Developer Community Team of two. Now that we were on a new team and had two new people joining our team, there was a lot to consider. There was a leveling component that needed to be carefully thought through. We had four community managers, one more senior than the other three. Two were working on community and community programs and the other two were specifically working on community for Developers, but also some developer marketing programs. We also had two open headcount for very specific roles on our team from the previous reorg, just a couple months before.

Each individual had to be carefully considered, starting with the new team members that came from another team. Jessica Langston (now Director, Trailblazer Community), who had been working at Salesforce for a few years at that point was the most experienced on my new team. She had been killing it in her role managing the developer community and developer marketing programs. She was doing a ton of really impactful work for the developer community through advocacy programs, events, community engagement, and so much more. Jessica was universally loved by the developer community and everyone internally. She was also managing a community manager, Mallory Ranahan, who moved to our team as well.

Mallory Ranahan (now Senior Community Manager) had also been at Salesforce a few years. She started as a developer program manager and then moved into a developer community management role. Mallory was also killing it in her current role, loved by the developer community, and deeply appreciated by her team. When Jessica was out for six months on Maternity leave, Mallory did an incredible job by taking on a huge load of work, continuing to engage, grow, and support the developer community. She learned a lot about community management during that time, and I personally believe that was a pivotal time in her career. No better way to support someone while they’re on leave than by making sure they come back to beautifully managed programs while they were away. Mallory did just that.

SIDE NOTE: I wrote a whole blog post about the amazing people I’ve hired. I like to believe that hiring those folks took some skill and hard work. Jessica and Mallory getting moved onto my team, well, that was just plain amazing luck. Both brilliant, high performing, fun team players who were and still are ready to take on anything. I can’t believe how fortunate I was to get these two exceptional humans on my team.

Jessica started reporting to me, and we moved our three incredible community managers to report to her. Jessica was the most senior on the team and had people management experience already, so this was a great opportunity to expand her role, especially since we already knew she was, like I said, killing it. At the time she joined our team, she and Mallory were still running some developer marketing programs, so we moved those off of their plates as soon as we could to clear the way for this new structure. Going from a manager of one to a manager of three means that we needed to give Jessica more time and flexibility to focus on community programs and supporting her team.

A few months later, we hired a couple more people onto the team, Tiffany Oda- to build and manage a specific program we were kicking off- and Kendall Odom- as a community coordinator to focus on community support. Now, I mentioned the silos created by a community manager specifically focusing on one program, so after the program got kicked off, we adjusted Tiffany’s role, and holy moly, am I glad we did. Hang tight and I’ll come back to that.

Things evolved for the rest of the team in a few different ways in terms of reporting structure, and most importantly, role definition. As I said before, the roles were too broad and weren’t clearly defined. That doesn’t feel great as a team member or drive great results as a team.

Nom Nom Nom. A Meaty Sandwich Served On a Delicious Role 🥪

I’m sorry you had to gnaw through so much superfluous bread up until this point, but we’ve finally arrived at the meat of the sandwich: role definition.

Everyone needs role definition, but it was especially important for our three community managers because they were technically in the same role. I had to come up with the right structure and focus that would give them career growth as well as make sure our team was operating in the best possible way.

One night, as per usual, I was trying to sleep, but I couldn’t stop thinking about work. I couldn’t stop thinking about the best path forward for these roles. An idea struck me at a ridiculous hour. I decided it was brilliant, so I sent myself a quick email from my phone and finally fell asleep. I can’t tell you how many “brilliant” ideas I have when I can’t sleep and I wake up the next day to the dumbest ideas you can ever imagine. Legitimately meshugenah ideas, but that’s ok, it’s just part of the process! ANYWHOODLE, the next day, I completely forgot my idea from the night before (this also happens to me all of the time). I opened my email and it took me a few minutes to figure out WTF I was saying to myself (another regular occurrence). The email said:




And this time, it wasn’t a completely ridiculous idea. This was it. Three focus areas we were constantly thinking about. Three community managers.

Hol up.

Would this work? Was there enough meat in each of these three focus areas to create these roles?

I really dug into each of the focus areas, mapping out our programs and the work that needed to be done. Turns out, the work in each of these focus areas wasn’t just enough for one role, but even more than one person could do on their own. It also created an opportunity for our community managers to develop and own initiatives and programs.

Besides creating fulfilling roles for each of our community managers, it gave them a specialization that could lead to career growth —

  • Learning more about the product, product ideation, and the product team
  • Growing knowledge around content, content strategy, and content distribution
  • Developing skills around engagement, moderation, mediation, and feedback

They had a path to grow even outside of the community field if they wanted, and they were able to take more ownership over the work they were doing. Focus areas FTW!

As for the other folks on the team, we adjusted Tiffany’s role to focus completely on ops, and like I said, holy moly. She took us from a two to a ten in how we operated, tracked, and measured everything we were doing. If by the time I left Salesforce we were at a ten, at this point she has broken the scale of measurement entirely. As part of Tiffany’s rise to operational fame, we promoted her. Kendall started reporting to her, also focusing a lot of her time on operations. That’s right, Community Operations is THAT important that I chose to dedicate 1/3 of my team to it. Moving Kendall to Tiffany’s team ended up being a stellar fit because Kendall was loving operations. She’s a natural when it comes to looking at a process and figuring out a way to improve it, and she was also able to have more ownership by leading different projects.

I Waved My Magic Wand And It All Worked Perfectly! 🧙🏻‍♀️

Bippity Boppity Who… does what again? There’s no magic wand. Sorry I lied to you. You can’t expect to restructure your team, completely change everyone’s roles, and have everything work perfectly right off the bat. There’s a transition period.

I carefully mapped out what I thought were the three most important things to note about this transition, and I walked my team through them before I went over the new role definitions. Here they are:

This isn’t a perfect science

There will be overlap and confusion from time to time. With a collaborative environment and strong communication, we can overcome these issues. We can make adjustments as needed.

We’re a team

These roles have been created in a way that will require dependencies on other members of the team. While everyone will have ownership, these roles necessitate and encourage collaboration across our Community team along with the Placement and Student Groups team. Everyone very clearly stated that they wanted more ownership over the work they are doing, and this plan allows for that, but everything we own individually is still collectively owned by our team.

There’s a transition period

This will not automatically all fall into place. There will be certain things that we’ll work closely on for a period of time before fully handing off. Let’s all approach these new roles with an open mind, and give this new structure some time to really work. Give me feedback along the way!

Everyone Loves A Good Org Chart

This is what ours looked like:

For an accessibility-friendlier version, comment below or ping me on LinkedIn and I’ll send your way.

Did Someone Say Free Samples? But We’re Not Even At Costco! 🆓

After sharing with my team the three important points about the transition, I walked through each of the new roles with sample role responsibilites and success metrics. Here’s a version of each of those:

And Did They Live Happily Ever After? 👸❤️👸🏾

This structure is mostly still in place after three years, which is pretty great. Honestly, it’s not the structure itself that’s most exciting to see, but it’s seeing the individuals in all of these roles really thrive. There’s been promotions, program/ initiative launches, and so much more that I’ve seen come from this awesome group. Will it eventually change? Of course! Like I said before, every team has to change and evolve as your business changes and evolves. For me however, I love how this structure worked out and where it took everyone. Was it perfect? No, but nothing really is. What matters is that you’re always moving in the right direction– a direction that allows both the business and your people to thrive.

Would love to hear your thoughts and questions. Share them below!



Holly Firestone

Community Strategist. Currently: CEO, Holly Firestone Consulting. Previously Venafi, Salesforce & Atlassian.