Fred Schwartz
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2025
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Fred Schwartz

Fred Schwartz

I'm an operations and strategy professional who specializes in stepping into complex, ambiguous environments and building the systems and processes that make companies function better. My work spans CRM architecture, billing operations, team leadership, product definition, and cross-functional execution across industries including construction, SaaS, healthcare, and early-stage startups.

Currently working at Cardstop as an early operator across product strategy, compliance, investor materials, go-to-market planning, and company building.

Ottimate (formerly Plate IQ)  ·  2018 – 2021  ·  Head of Billing

Turning $500k+ of outstanding AR into a structural fix

$500k+
Total AR at start
$700k+
Recovered in under 9 months
8
Projects launched

When I joined the billing team, accounts receivable was growing with no clear understanding of why. I was tasked with collections — but my goal was larger: understand the root causes, fix the process, and prevent the problem from recurring.

01  ·  The Problem

Over $500k owed by 400+ customers — with no clear picture of why

The company had a growing AR problem but no structured analysis of what was driving it. Collections was being handled reactively, without data, segmentation, or a prioritization strategy. Before any money could be recovered, the data needed to tell a story.

$500k+
Total outstanding AR
400+
Customers with outstanding balances
0
Existing systems to flag or prevent it

The first step was to stop treating all AR as the same problem. I segmented the data three ways: by dollar value per customer, by how many months the balance had been outstanding, and by the likely difficulty of collection. Each lens revealed something different.

02  ·  The Analysis

Three lenses. One clear picture.

AR Value by Priority Segment
$500k+ TOTAL AR
High Priority (≥ $10,000)
5 customers driving ~63% of total AR
$315k63%
Med Priority ($500 – $10,000)
130 customers
$160k32%
Low Priority (< $500)
265+ customers
$25k5%
Key finding
63% of total AR traced back to just 5 customers. The problem was concentrated, not distributed.
AR by Difficulty to Collect (Months Outstanding)
Easy
$270,000
110 customers1–3 mo.
Moderate
$145,000
60 customers4–6 mo.
Difficult
$85,000
230 customers7–12 mo.
The strategic opportunity
The top accounts in the Easy and Moderate segments represented the majority of recoverable AR. Focusing collections here first generated the fastest returns with the least friction.
03  ·  Root Cause Analysis

The AR wasn't a collections problem. It was a process problem.

After segmenting the data, I interviewed customers and internal teams to understand why balances were outstanding. Four root causes emerged — each requiring a different fix.

Primary cause
Payment method onboarding was broken
New customers struggled to connect a payment method through ACH. The process required micro-deposits, was prone to failure, and had no system to flag or follow up on failures. Many customers wanted to pay but simply could not get through the process.
Primary cause
Legacy client billing was entirely manual
A subset of older clients were billed via custom spreadsheets calculated and sent manually. The process was slow, error-prone, and frequently broke down — creating AR that had nothing to do with willingness to pay.
Primary cause
Payment method failures went undetected
When a payment method failed, no one was notified — not the billing team, not the customer. Balances accumulated for months before anyone knew. There was no automation, no alert, no retry logic.
Secondary cause
A small group held payment over product issues
A minority of customers were withholding payment due to product dissatisfaction. While real, this was the smallest driver of AR — and the one that required product-side fixes rather than billing-side ones.
04  ·  What We Built

Eight projects. Each one tied to a root cause.

The analysis produced a clear action plan. Every project mapped back to a specific finding — nothing was added speculatively.

01
Plaid via Stripe implementation — Replaced the broken ACH process with Plaid, allowing customers to connect payment methods using their bank login. Nearly eliminated payment method failure for new customers.
02
Focused collections on highest-priority accounts — Directed all collections effort toward the Easy and Moderate segment accounts with the largest outstanding balances. Generated $400k+ in recoveries within the first 3 months.
03
Legacy client billing redesign and renegotiation — Documented and overhauled the manual billing process. Discovered pricing structures were costing the company money. Renegotiated all legacy contracts, adding true MRR.
04
Payment failure automation — Built automations to alert billing team members and customers when a payment method failed, with a direct link to update it. Eliminated silent AR accumulation.
05
Commission matrix redesign — Restructured commissions so sales reps were only paid after customer payment was received. Created direct incentive for reps to assist with collections.
06
Contract language update — Revised contract language to clearly communicate invoice due dates and that autopay was a requirement — reducing ambiguity that customers had used to delay payment.
07
Account deactivation tool redesign — The original tool deleted all users on deactivation, making reactivation impossible. Rebuilt it to freeze accounts while preserving user data, enabling instant reactivation and making deactivation a credible collections lever.
08
Salesforce / SaaSOptics integration — Connected Salesforce to SaaSOptics to surface invoice payment status directly in the CRM, giving the team real-time visibility across systems.
05  ·  Results

$700k+ recovered in under 9 months. Structural AR problems eliminated.

$700k+
Recovered in under 9 months — including $400k+ in the first 3 months alone — reducing the overall AR problem by approximately 90%.
Near 0
New AR from payment method failure after Plaid implementation. Almost all new customers had an active payment method on file from day one.
True MRR
Legacy client renegotiations converted dynamic, unreliable billing into true monthly recurring revenue — improving both cash flow and reporting accuracy.
The bigger lesson
The AR wasn't a collections problem. It was the visible symptom of broken onboarding, broken billing infrastructure, and misaligned incentives. Fixing collections without fixing those would have been collecting water with a leaky bucket.

Notes

Opinions on tools, processes, and frameworks I've used across operations, billing, and company-building. Everything here is based on real use — not theory.

ClickUp: Why I Sunset Jira and Confluence to Replace Them With It

ClickUp is one of the first tools I used where I really saw the difference between a tool that is technically powerful and a tool people will actually use. Here's why I sunset Jira and Confluence to replace them with it.

ClickUp logo

When I first started at Audicus, I followed my usual approach: interview people across departments and take stock of the existing tech stack before touching anything. One of the first things I noticed was that SOPs were all over the place. There was no standardized way of documenting processes, and no project management software was actually being used day to day.

When I dug a little deeper, I realized the company already had Jira and Confluence licenses. Nobody was using them. I pulled the cost of those licenses and realized we were paying real money every month for tools that had effectively become shelfware.

I had come across ClickUp through a YouTube channel I watched, so I compared its features and capabilities against what we actually needed. It was cheaper than what we were already paying for, and it could technically do everything Jira and Confluence were supposed to be doing for us.

ClickUp Docs interface showing how to add pages and subpages
ClickUp Docs makes it easy to organize documentation with pages and subpages.

On paper, Jira and Confluence made sense: Jira is a strong project management tool, and Confluence is a strong place to build SOPs and internal documentation. But neither one had actually become part of how the team worked. People weren't consistently creating tickets, and SOPs weren't living in one clear place. The company was paying for software with real value in theory, but it had quietly become shelfware.

That's one of the most common problems with internal tools: the platform can be powerful, but if people don't understand it or feel like it makes their work easier, it never gets adopted.

Within my first three weeks, I made the decision to sunset Jira and Confluence and implement ClickUp instead.

That might sound like a big change, but the actual rollout moved quickly. Within roughly the next week or two, while still handling my normal responsibilities, I onboarded the entire company of 50+ people into ClickUp.

The reason that worked was simple: ClickUp was approachable.

It gave people a clear place to create tasks, assign owners, manage due dates, organize projects, and document processes without needing a heavy amount of training. It felt more modern, more flexible, and less intimidating for teams that were not already deeply familiar with tools like Jira or Confluence.

Small operational win

I replaced an underused tooling setup, reduced unnecessary complexity, and helped onboard 50+ people into a new operating system for work in a matter of weeks.

Why ClickUp worked for SOPs

ClickUp Docs search showing a page result inside a document
Pages inside ClickUp Docs are easy to search, which matters when documentation starts to grow.

For SOPs, ClickUp Docs became especially useful.

ClickUp Docs can be organized with pages and subpages, which makes it possible to create a real internal handbook structure instead of one long document or a messy folder of disconnected files. ClickUp also has a Docs Hub, where teams can organize, search, and create Docs and wikis from one central place.

That matters because SOPs are only useful if people can actually find them.

In ClickUp, a team could have a high-level Doc for a department, then break that Doc into pages for different processes. For example, an Accounting Ops Doc could have separate pages for invoice processing, AP workflows, month-end close, vendor setup, approvals, and internal controls.

That structure made the documentation feel more like a living internal handbook than a pile of files.

It also made search easier. You could search inside Docs, use the Docs Hub, or use ClickUp's broader workspace search to find items you had permission to access. That is a big part of what makes documentation useful in a real company environment: people should not need to remember where something lives. They should be able to search for it and get to the answer quickly.

Example ClickUp SOP document with nested pages and a process document open
An SOP in ClickUp can include pages, comments, relationships, formatting, and ownership context.

The other thing I liked about ClickUp Docs is that they were not just static pages.

You could use comments, formatting, cover images, tags, page organization, sharing permissions, and relationships. You could also connect Docs to tasks, which is what made the tool especially useful operationally.

That is where ClickUp became more than an SOP library.

A process could be written in a Doc. A task could be created from that process. A manager could assign ownership. Someone could leave a comment, ask a question, update a step, or connect the Doc to related work.

The documentation and the work were no longer completely separate.

That was the real value.

My take

This experience shaped how I think about operations tools.

The “best” tool is not always the most advanced tool. Sometimes the best tool is the one that gives the team enough structure without overwhelming them.

Jira can be excellent when you have the right workflows, the right team, and someone who knows how to manage it well. Confluence can be excellent when a company is committed to documentation and has a clear knowledge management culture.

But if a company is earlier in its operational maturity, or if the immediate goal is adoption, ClickUp can be a much easier starting point.

It gives teams a simple way to answer the basic questions that matter: what are we working on, who owns it, when is it due, where is the process documented, and what needs to happen next.

That is why I still like ClickUp. It is flexible enough to handle real work, but approachable enough that people can actually get started.

For me, that combination is what makes a tool operationally useful.

I still use ClickUp today for personal projects, planning, and keeping track of different things I am working on. It is not because I think every company should use ClickUp for everything. It is because I have seen firsthand how much value a tool can create when it lowers the barrier between “we should be more organized” and “we are actually using a system every day.”

Note: I am not affiliated with ClickUp. I just like the product and have used it firsthand in a real operating environment.

Salesforce: The Most Powerful Tool Most Companies Use Wrong

Salesforce gets blamed for being complicated. In my experience, the complication usually comes from how it was set up, not from the platform itself.

I’ve been a Salesforce admin at two different companies. Both times, I inherited a setup that had grown organically — fields nobody used, workflows nobody understood, and a general sense that the CRM was something the sales team had to deal with rather than something that helped them.

The biggest mistake companies make with Salesforce is treating it as a recording tool rather than a decision-making tool. If the only thing your CRM does is log calls and store contacts, you’re not using it — you’re just paying for an expensive Rolodex.

The unlock happens when you start designing Salesforce around how your team actually works: what decisions do they need to make, what information do they need to make them, and how do you surface that at the right moment? At Ottimate, connecting Salesforce to SaaSOptics to show invoice payment status changed how the sales team engaged with collections — suddenly they had context, and that changed behavior.

Best for: Any company serious about revenue operations. The ROI is real, but only if someone owns the admin work properly.

Watch out for: The cost scales fast. Before you add another license or another module, ask whether you’re actually using what you already have.

Plaid Changed How We Onboarded Customers — Overnight

ACH payment setup used to be one of our biggest sources of AR. Then we implemented Plaid. The drop in failed payments was immediate and dramatic.

Before Plaid, connecting a bank account to our billing system meant micro-deposits — a process that took days, confused customers, and failed constantly. The UX was bad enough that customers who genuinely wanted to pay simply gave up. That became AR, and AR became a collections problem.

Plaid via Stripe changed that completely. Customers log in with their bank credentials, verify instantly, and are connected. The whole process takes under two minutes. After implementation, nearly every new customer had an active payment method on file from day one.

The thing I’d emphasize to anyone evaluating Plaid: it’s not just a UX improvement. It’s a structural fix. You’re not making the same broken process faster — you’re replacing the broken process entirely.

Best for: Any SaaS company collecting payment via ACH. If you have AR problems and you haven’t looked at your payment method onboarding, start there.

Watch out for: Make sure your team understands how the Stripe integration works before going live. The setup is simple, but the configuration details matter.

In Defense of Spreadsheets: When to Use Them and When to Stop

Spreadsheets have a bad reputation in certain tech circles. I think that’s wrong. A well-built spreadsheet is one of the most powerful ops tools in existence.

The knock on spreadsheets is usually that they don’t scale. That’s true — but scale isn’t the point of a spreadsheet. Speed and flexibility are. When you need to analyze something fast, test a hypothesis, or build a one-time model, nothing beats a spreadsheet.

The mistake is using spreadsheets as a permanent system instead of a diagnostic tool. A spreadsheet that tracks customer data for two years and is emailed around every week isn’t a spreadsheet — it’s a poorly designed database. At that point, you’ve grown beyond what the tool is good for.

I’ve used spreadsheets to build the first-ever AR analysis at Ottimate, to model legacy client billing, to prototype commission structures, and to track office move logistics. Every one of those was the right tool for the job at that stage. The skill is knowing when you’ve outgrown it.

Best for: Analysis, modeling, one-time projects, and any situation where you need answers fast and the data isn’t going to live there permanently.

Watch out for: The moment multiple people are editing the same spreadsheet regularly, it’s time to build something more permanent.

Jira for Non-Engineers: Getting the Most Out of It When You’re Not on the Dev Team

Jira is built for engineering teams, but operations leaders who ignore it are leaving visibility on the table. Here’s how I use it.

Jira has a reputation for being complicated. That reputation is mostly earned — but the complexity exists for a reason. At its core, Jira is an extremely flexible system for tracking work through defined states. That flexibility is exactly what makes it powerful for cross-functional ops work.

At Cardstop, I use Jira to manage product and engineering work. Coming from an ops background, the key for me was learning to think in tickets: every piece of work needs a clear definition of done, an owner, and a status. That discipline makes standups faster, makes blockers visible, and makes the relationship between ops and engineering much smoother.

For non-engineers, the most useful parts of Jira are the board views, the dependency tracking, and the ability to link bugs to business impact. If you can frame a bug as “this is causing X% of customers to fail at step Y,” engineers prioritize it differently.

Best for: Any team that ships software, especially when ops needs to stay in sync with engineering without being in every meeting.

Watch out for: Jira can become a ticket graveyard if nobody owns backlog hygiene. Regular grooming sessions are not optional.

How I Approach a New Company: The First 90 Days

Every company I’ve joined, I’ve used a similar approach to get oriented fast: audit, interview, prioritize, ship. Here’s what that actually looks like.

The biggest mistake people make when joining a new company is moving too fast toward solutions before they understand the actual problem. The first thing I do at any new company is audit — tools, processes, data, and people. Not to judge, but to understand what exists and what the gaps are.

The interview phase is just as important. You learn things in a 30-minute conversation with a customer success rep that you’ll never find in a dashboard. People closest to the work know where the friction is. The goal is to collect those signals before they get filtered through organizational hierarchy.

After the audit and interviews, I prioritize based on a simple question: what’s causing the most pain with the highest leverage? At Audicus, that was Confluence adoption. At Ottimate, it was AR. At Cardstop, it was the lack of a structured operating model. Each time, the answer came from the audit, not from assumptions I brought in from the outside.

The shipping phase matters most. Insight without execution is just observation. The credibility you build in the first 90 days comes from shipping something real — even if it’s small — and making it stick.