Sherpa: From Financial Blindness to Unit-Level Financial Modeling

Meet Ben Nowlan:

Ben Nowlan, CEO of Sherpa, is a founder with over 20 years of experience leading startups and solving retail challenges through technology. Based in Australia, Sherpa has become a market leader in last-mile retail fulfillment — serving national retailers with same-day and on-demand delivery.

Over the past decade, Ben has navigated growth, fierce competition (including from Uber), and the unique economics of Australian labor markets — all while building a solution that helps independent retailers compete with giants like Amazon.

The Challenge

Sherpa faced a sudden leadership crisis when their in-house CFO suffered a serious illness. This left the business financially blind — two months of unreconciled transactions, no real-time view of cash flow, unit-level margins, or working capital, and major governance risks.

This came during a high-pressure phase:

Managing millions of transactions each year
Facing margin-sensitive competition from global players
Preparing for a merger and business turnaround
Needing to make hourly operational decisions on pricing, marketing spend, and AR/AP

The Approach

Cypher stepped in to restore clarity and control fast. The work included:

Forensic financial cleanup of two months of unreconciled data
Building unit-level financial models and scenario-based forecasts
Embedding forecasting into daily operations so Sherpa could make hourly decisions on pricing, spend, and margin protection
Optimizing accounts receivable and accounts payable processes
Supporting merger modeling and shareholder reporting with clean, investor-ready financials

Cypher’s approach combined technical financial acumen with practical CFO insight, giving Sherpa not just accurate numbers — but the ability to act on them in real time.

The Outcome

With Cypher’s support, Sherpa:

Regained financial visibility and control
Reduced operational headcount from 60+ to less than half while maintaining delivery volumes through automation and AI-powered driver support
Increased gross profit margins by 2–3 percentage points, translating to hundreds of thousands of dollars
Developed real-time decision-making capabilities to adjust pricing, marketing, and operational priorities instantly
Gained the confidence to make margin-sensitive calls during competitive pressure and a corporate turnaround

If you’re ready to go from financial chaos to real-time control like Sherpa did, let’s connect.

Build your empire—we’ll crunch the numbers. — Courtesy of Cypher

Who we are

01 The Challenge

Sherpa lost its CFO and lacked access to reliable financial data during a critical phase.

02 Our Approach

Cypher reconstructed the financials, built unit-level forecasts, and provided strategic financial insights.

03 Implementing the Solution

We embedded forecasting into daily operations, enabling hourly decisions around margin, pricing, and spend.

04 The Outcome

Sherpa gained visibility, control, and the confidence to invest in growth during a business turnaround.

“I haven’t come across a firm that’s better than Cypher. For any founder, especially young ones — having that CFO time to truly understand your P&L, balance sheet, and decision levers is invaluable.“
— Ben Nowlan, CEO at Sherpa