Joss Poulton

SaaS Subscription Management & ARR Reporting in Salesforce Using Rollup Helper

May 6, 2025 / Joss

SaaS companies approach integrating subscription management data, including MRR/ARR tracking and reporting, into their CRM differently based on their GTM model (PLG, sales-led, hybrid), stage of life, product complexity, and existing business/billing systems.

If you have the luxury of being a sales-led business with a healthy ACV and fairly low order volume, you can create a robust subscription management system within Salesforce using just Rollup Helper (currently $1560/org/year for unlimited rollups – there are so many other great use cases!) and a custom Subscription object, which we did successfully at UserGems.

How we did it:
In this solution, the Opportunity Product becomes the source of truth:

Fee Type is either one-time or recurring, based on the Product, but can be overridden
Revenue Reason tells us whether the revenue is New Business, an upsell, downsell, or a renewal (if there is both a downsell and a renewal, there would be two line items)
Start & End Dates tell us when the ARR for this instance of the product is valid. The end date needs to be one day before the effective date of any changes to the subscription to avoid double-counting.
Current ARR is a formula field that looks at the Fee Type/override, the product dates, and decides whether to call the Sales Price ARR as of this moment
OLI Total ARR represents the total ARR on the line item, regardless of whether it’s active (aka “Current”) or not. OLI stands for “Opportunity Line Item,” another term for the Opportunity Product.

The Opportunity rolls up key ARR and OLI data that is useful for sales deal reporting:

The Opportunity then rolls up to the custom Subscription object, which can roll up currently active ARR and product data from one or multiple Opportunities, along with the complete history of all changes to ARR:

The Subscription object then rolls up to the Account:

- We can see the Current ARR on the Account, which can be from one or multiple subscriptions. We can also roll up other product limits and entitlement data from the OLIs, for example, the number of units active shown above.

Rollup Helper Considerations: When designing the rollups, it’s helpful to use both real-time and scheduled nightly rollups at all levels. For the nightly rollups, follow the chain of rollups to reduce data delays (e.g., have the OLI > Opportunity rollup run an hour before the Opportunity > Subscription rollup, which runs an hour before the Subscription > Account rollup).

Why it made sense for us:
The custom object + Rollup Helper solution fit the bill well for our situation. We had hundreds of customers with high-value subscriptions, which they amended 1-2x per year. Customers were being quoted manually via a well-documented process using Google Doc templates and an approvals Slack channel.

The system worked well enough, even with a dozen sellers. The alternatives are almost universally more frustrating, heavy-handed, and costly, often forcing sellers through complex workflows, requiring .5-2x dedicated Sales Ops headcount, and slowing down the business’s ability to experiment with its pricing and packaging and product catalog.

What did our homegrown subscription management system get us?

✅ A Finance Dashboard within Salesforce showing things like:
- Current ARR against goal
- Future-dated committed ARR
- Currently Active ARR by Product
- ARR change by month by Revenue Reason (New/Upsell/Cross-sell/Downsell/Churn)
- NRR reporting across the install-base
- Trailing 1-year ARR growth %
✅ Current MRR & ARR data by Salesforce Account
✅ Historical MRR & ARR change reporting by Salesforce Account
✅ Support for multiple subscriptions per Salesforce Account (with Account-level ARR rollup)
✅ A system that updates in real-time but also trued itself up nightly via scheduled jobs
✅ A system that was ultimately driven by Sales + Renewal Opportunity Products, making our sales and renewal data the source of truth for MRR/ARR within Salesforce
✅ High-quality data we trusted to run sales commission reporting

What didn’t it get us?

(1) We didn’t build the slick guided sales workflow that CPQ systems aspire to — instead, we documented the sales process in Notion/Guru and created a step-by-step approvals worksheet and order templates that sellers cloned and filled out for each deal.
(2) We didn’t get to building an integration with our accounting system to audit and align data or bring invoice and payment data into Salesforce.
(3) We didn’t integrate sales tax with quoting — but our prospects didn’t seem to mind the disclaimer that they might be invoiced sales tax not shown on the quote.

Turning RevOps Firefighters Into Design-builders

July 13, 2022 / Joss

Houses Needing Repair A few months ago, a colleague asked me to describe a typical day working in Revenue Operations. I said that right after my iced triple (non-negotiable) “I check email/slack for any urgent support or requests and immediately lose control of my day.” I was half-joking, but the reality is that a day in the life of RevOps can be as unpredictable as a firefighter’s. The interesting part is, it’s not their fault.

I’ve observed that the great RevOps teams operate more like design-builders, who aren’t putting out one fire and leaving the ruins for the next but are methodically building, renovating, and beautifying what’s around them. At first, one or two areas get built out, and then they start to connect to each other — until finally, a well-planned neighborhood emerges and growth and happiness follow.

The most important thing that a company can do to enable a RevOps team to be successful isn’t actually to hire a design-builder over a firefighter. It’s to define success by having a clear and adopted goal-setting process at both the company and departmental levels. With clear goals in hand, RevOps teams can focus while funneling large new asks into the backlog for the next planning process.

An absence of clear focus creates silos, power struggles, bureaucracies, infighting, and way too many meetings as everyone pushes their own agendas. RevOps ends up in the middle, implementing half-baked solutions that then are stitched together, leaving employees and customers pulling fire alarms left and right. Next time you see your firefighter, give them a high-five! And next time you see your leadership team, ask them how those goals are coming along 😉.

Zuora’s SaaS Go-to-market Mistakes & Path Forward

February 9, 2021 / Joss

Zuora is a subscription management software company that’s been around since Bush was President — founded in 2007, three years before Stripe and five years before Steelbrick. In addition to its head start in the niche world of subscription management and billing, Zuora has a good pedigree, with a Founder/CEO, Tien Tzuo, who was employee #11 at Salesforce, serving as CMO and Chief Strategy Officer in its heydey of growth (1999 – 2007). Tzuo felt many of the pains in trying to run Salesforce on Salesforce that other subscription companies did, and he decided to do something about it.

Subscriptions aren’t just for software companies and have been around for a long time (think newspapers and insurance). They’re a living/breathing thing that’s especially hard to manage in a multi-product and self-service world where people don’t wait until their renewal to make changes, and companies constantly want to sell, upsell, cross-sell, and discount things in new and creative ways to promote their products and support their customers across channels — actions that create anomalies and data challenges left and right.

Zuora seemed prime for massive success…so why is it that this company that seemed destined for greatness in an exploding industry is doing just ok compared to its peers, coasting around a $2B market cap while newer competitors like Stripe are worth $100B+ and are growing faster with more scale? Facing additional pressure, Salesforce, a key ecosystem partner, has turned its 2015 $300M Steelbrick acquisition into a major player competing directly with Zuora and likely already far surpassing it in adoption.

By the mid-2010s, Zuora was known to have a pretty slick sales pitch and I’ve worked at two companies that have purchased its products. It’s been fun to watch their journey as a company and vendor. I have to hand it to their sales team, they do an excellent job selling into the back-office (go figure, they have budget), where they solve many problems for the modern SaaS CFO — problems that are unfortunately solved at the expense of the overhead that the platform brings.

Zuora tends to sell to enterprise companies and puts a lot of weight on system administrators, implementation consultants, developers, and an order management team — and has a host of products that are useful, but are often huge upsells with complex implementations. It’s a platform where everything is technically customizable and configurable, but nothing is pre-packaged or ready to go out-of-the-box even for the simplest of use cases, and mandatory implementation consultants are used as a crutch.

Stripe, on the other hand, works out of the box to the developer (its key persona that it obsesses over) and has nailed its user experience in being at the same time both technical and simple to the point of being considered elegant to all but the CFO and Controller. It’s easy to see why Zuora was left in the dust, especially considering its pricing model, which takes a percentage of revenue, and its less-than-straightforward implementation process, both of which put the company at odds with the same CFO they sold to so well.

All that said, I own shares of Zuora and believe in its future in one form or another. It’s one of the only pure-play subscription management companies out there, which is an industry I believe will grow exponentially in the next 10 years given fundamental changes in consumer behavior and the lifetime value that even a small subscription creates to a business. Zuora has also seen success in certain verticals without doing much to customize its product for them which is exciting.

One of the most interesting and tantalizing aspects of its potential to me as a shareholder is its current capital structure and financial performance, which reflects a lack of confidence in its own business model. The company is cashflow neutral (a positive rarity for a SaaS company of its size), growing at 15% (slow for its size), doing $300M in annual recurring revenue at a solid almost-100% dollar retention. I believe its valuation suffers because it’s neither considered a growth company nor a cashflow positive well-established company, but is stuck somewhere in between, in limbo. Investors, like its customers, have no idea what to make of it and its future but want to believe in it because it kind-of-works and has a vision that’s easy to get behind. If Zuora knew how to grow its sales reliably and efficiently, it would make those investments and sacrifice profitability for growth, which today’s market would reward it for handsomely, but instead, it seems paralyzed and keeps chugging along, becoming more self-reliant but also less prominent every day.

The worst-case scenario to me as an investor is still a win. One of many potential suitors (eg. Microsoft, SAP, Oracle, Salesforce, or Stripe) could pay a premium to acquire the powerful platform, 1k great and sticky Enterprise customers, and $300M worth of cashflow neutral ARR off the public market to pump their own growth rates with, along with their ability to cross-sell products with its customer base. I could easily see a $3.5-4B acquisition happening this year that would be fair to both parties, as Zuora would enter the negotiations in a position of relative strength since it doesn’t need cash or a sale to carry on with its aspirations.

The best-case scenario is that Zuora stays independent and claims its rightful throne in the Cloud, which is also much more fun and exciting to think about, especially at a time when they’ve just brought in (another) new Chief Product Officer.

If I were the Zuora leadership team, I would:

(1) Start Selling Solutions instead of a dream. 14 years in, there’s no excuse for not being able to take a customer live selling a handful of simple subscription products in a week instead of three months. They should be able to do it themselves and it should be as frictionless as answering a questionnaire around how your business sells things and what your finance, accounting, and operations teams’ requirements are.

Beyond simplifying go-live, customize the platform for a handful of verticals where there’s traction by templatizing an implementation from the start and delivering key metrics, data, and reporting that vertical companies care about.

(2) Stop charging customers for training. It’s mind-boggling to me that a company with a product that it knows is hellish to implement charges thousands of dollars for access to a seat of training resources. They’re punishing people who they should be courting as potential evangelists….sorry for man-splaining how subscription customer success works to Zuora, but I can’t resist! Don’t put up unnecessary barriers trying to squeeze more money out of the people stuck trying to figure out your software, which doesn’t explain itself.

(3) Open up and simplify APIs using Stripe as a template of what to aim for. Give developers self-service free test environments without talking to a six-legged sales team and a Regional VP.

(4) Better-align Pricing with Value and focus on vertical-based pricing that, for example, includes an easy way for a new SaaS startup with scale in mind to buy a slimmed-down version of the product (which dovetails with #1 and #3), setting them up to become an Enterprise customer of the future. Zuora’s attitude needs to change from “we allow companies to start small” to “we obsess over making small customers successful via self-service.” Their Enterprise Account Executives might hate them in the beginning, but they’ll come to realize that strategy will make things better for everyone.

Bonus: Take a leaf out of Profitwell’s book (they built ‘the Robinhood of SaaS analytics’ for Stripe that’s easy to use and delivers value instantly). It would be guaranteed to make the CFO very happy.

Should SaaS Business Operations be Centralized?

February 8, 2021 / Joss

Since business operations stakeholders typically represent most departments within an organization, as a company grows, it’s natural to question and re-question how to structure your team and efforts. Sales, marketing, customer success, product, and finance are often groups with very different and sometimes conflicting agendas and timelines. For example, early on, sales might want to sell a deal that involves customizing a product and structuring a multi-year deal to suit a specific customer’s needs — while finance and accounting teams are frantically googling revenue recognition rules and are figuring out when the right time is to make the product team stop innovating and start implementing a sophisticated sales tax solution.

Ops teams are often stuck in the middle, trying to bring order to chaos and move things forward. An axiom that I try to live by at this stage is to be bold where appropriate and to try to avoid uninspired compromises, especially in architectural decisions. In order to do that, communication and transparent prioritization and backlog grooming are critical. A good business operations team can rise above system administration, and articulate a clear plan to enable go-to-market teams to achieve their goals, or sometimes just help to set some together. A monthly stakeholder meeting is a good format and cadence to drive an agenda.

The earlier your company is in its go-to-market efforts, the more oriented your business operations team will (and should) be towards sales. Early on, there typically isn’t a separate sales ops function, and companies often make their first dedicated business ops hire. The CRM and marketing automation design decisions that get made need to be thoughtful and should try to toe the line between iterating quickly and building for scale. I would argue that centralization at this stage is critical since things are moving quickly and the customer journey needs to be stitched together (sometimes with duct-tape) by people who understand its daily evolution.

Given that contradictory agendas between departments tend to grow along with the business, there comes a time when sales, marketing, and finance all want their own operational hires solely dedicated to their function. There isn’t a one-size-fits-all answer as to whether that’s the right decision, but if a department is advocating for its own ops hire, it’s crucial that the department leader articulate why that decision is being made, and to pre-negotiate what that new hire’s relationship will be with both groups ahead of the interview process. It might seem obvious, but the interview process should include the centralized ops leader who is in a position to qualify the candidate technically and is someone they will need to have a strong relationship with. Expectation setting is so important, for your new hire and for the department from whom you’re asking to hand over the virtual keys.

The biggest mistake that a company can make is to decentralize operations as a way of consoling a department leader who wants to ‘go rogue’ or because lines of communication are fractured between groups. What might look like a way to appease everyone in the short-term might actually be setting yourself up for failure. With good expectation setting, dotted-line reporting can also work very well, where a departmental ops hire still attends centralized operations team meetings and holds a weekly 1:1 with a point person on the dedicated ops team.

Why You Should Join a Non-Profit Board Early in Your Career

September 10, 2019 / Joss

dogs in a boardroom When interviewing people in the tech startup world and in speaking with friends, I’ve found that the mission of an organization almost always comes up as a key motivator for taking a job. So much so that it’s often up there with compensation and career development in terms of priorities. If we have the luxury of choice, we want to feel like we’re part of something larger than ourselves that we really care about (and even better if we can help make the world a better place while doing it). Helping non-profits is a great way to achieve that goal, while also bettering yourself and society.

At my day job, we make software that helps engineers and designers do their job better, easier, and faster. In addition to selling commercial software to professionals, we also give away free cutting-edge software to students and hobbyists. People use our software to do some pretty amazing things, which motivates and inspires us and helps us attract candidates and retain employees.

Outside of work, I’ve also always enjoyed volunteering and giving back to the communities in my life. In general, I value opportunities to gain different perspectives, grow as a leader, learn from others, network, and make new friends. I’ve found all of those things and more in joining a nonprofit board over the past eight years.

When we think of non-profit boards we often think of a bunch of people maybe late in their career, retired, or who don’t need to work — sitting around a table combing through financial statements, writing big checks, and asking their friends for donations. While that can be the case, most nonprofits are small and have ‘working boards’ that actively support the organization day-to-day while also setting a long-term strategy and thinking about the 10,000-foot view. At the Providence Animal Rescue League (PARL), the board does all sorts of things, from helping run fun and engaging events, to making connections with local businesses, to supporting our Executive Director when they’re looking for guidance on something that’s in our wheelhouse.

I think of my non-profit board service and progression in leadership roles as the best MBA that I could have asked for, while also helping to save a few thousand incredibly cute animals along the way. The organization struggles with a lot of the same things that we do at my day job (what’s our mission and how should it and we evolve? who is our target customer? how can we effectively communicate what we do and stand out?). I’ve often been able to apply things I’ve learned and done to my corporate job — including valuable transferrable skills such as budgeting, recruiting, and people management — not to mention cat herding. It’s a give and take where both organizations benefit, and so do I.

Think about what you’re passionate about, whether it’s something like animal welfare, the environment, helping those less fortunate, or staying connected to an institution that you used to be a part of (eg. alumni association boards) or even small organizations in the town you grew up in or a less affluent part of town. If you’re stuck, there are some great directories of non-profits such as Guidestar that can help you brainstorm.

Non-profit board service can take many forms with different levels of commitment. A great place to start is joining a board committee, which you can often do without (or prior to) joining a full board. For example, at PARL we have Marketing, Animal Welfare, and Finance Committees which have time commitments starting at around an hour per month. Whether you dip your toe in the water or go all-in, joining a non-profit board has so much to give — and hey, you might just make the world a better place while you’re at it.