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.

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

Turning $452k of outstanding AR into a structural fix

$452k
Total AR at start
70%+
Collected in month one
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

$452,400 owed by 200 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.

$452,400
Total outstanding AR
200
Customers with outstanding balances
12 mo.
Sample data period
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
$452k TOTAL AR
High Priority (≥ $10,000)
5 customers driving 63% of total AR
$285k63%
Med Priority ($500 – $10,000)
102 customers
$145k32%
Low Priority (< $500)
93 customers
$23k5%
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
$246,600
96 customers  ·  1–3 mo.
Moderate
$130,500
42 customers  ·  4–6 mo.
Difficult
$75,300
62 customers  ·  7–12 mo.
The strategic opportunity
The top 10 in Easy + top 10 in Moderate = 20 customers = $332,400 = 73% of total AR. This became the foundation of the collections strategy.
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 top 20 accounts — Directed all collections effort toward the 20 customers representing 73% of AR ($332k). Resulted in over 70% of total AR collected in the first month.
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

Over 70% recovered in 30 days. Structural AR problems eliminated.

70%+
Of total AR collected within the first month of the focused collections strategy.
$330k+
Recovered in the first month alone — 73% of total AR — by focusing collections on the top 20 accounts identified in the analysis.
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.