Customer Support & Operations Lead

Customer Support & Operations Lead Hello Cashflow Full-time · Remote (NZ-based preferred)

About Hello Cashflow Hello Cashflow exists to eradicate cash flow stress for small business owners. (see hellocashflow.com)

We are a plug-in that connects to Xero and QuickBooks, helping business owners, bookkeepers, and accountants understand their numbers without spreadsheets, jargon, or anxiety. We transform accounting data into clear, visual insights so business owners can make confident decisions.

We are a fast-growing SaaS startup with a small, sharp team of 10–12 people and around 500 customers. We are entering a major growth phase with plans to scale 10X. This is our first full-time customer support hire and a foundational role in how the business scales.

The Role We are looking for a highly organised, detail-driven Customer Support & Operations Lead who can confidently own the day-to-day customer experience.

You will be the first line of defence for customer questions, issues, and confusion. You will resolve the majority of support independently and use sound judgement to escalate only what truly needs escalation.

This role is about calm judgement, clear communication, and strong ownership.

You will work closely with: 👉 Business owners 👉 Accountants and Bookkeepers

You will also act as the filter between customers and the wider team.

This is a work-from-home role. Alongside weekly team meetings, we run semi-regular team retreats that require 2–3 days of travel. All costs are covered and they are genuinely a lot of fun.

What You Will Be Responsible For

Customer Support & Issue Resolution 👉 Resolving the majority of customer issues independently 👉 Communicating clearly and calmly with business owners and financial professionals 👉 Explaining financial or accounting concepts in plain English 👉 Using AI tools, video emails, and screencasts to resolve issues efficiently 👉 Jumping on Zoom calls when needed to unblock customers quickly 👉 Supporting customers who may be stressed, confused, or under pressure

Escalation & Judgement You will be trusted to know what to handle yourself versus what to escalate, including: 👉 Data integrity issues such as incorrect syncing or missing data 👉 Financial discrepancies and accounting edge cases 👉 Identifying whether an issue is a product bug, a user misunderstanding, or an accounting setup issue

When escalating, you will provide: 👉 Clear written summaries 👉 Screenshots or short videos 👉 Relevant context 👉 Proposed next steps

CRM, Systems & Organisation 👉 Owning CRM accuracy with high attention to detail 👉 Tracking conversations, follow-ups, and unresolved edge cases 👉 Ensuring no customer falls through the cracks 👉 Creating and improving internal support processes and documentation 👉 Building systems that will scale as customer numbers grow

Onboarding & Customer Experience 👉 Supporting new customers through onboarding 👉 Proactively following up when customers stall or disengage 👉 Continuously improving the customer journey based on real usage

Internal Coordination & Strategic Thinking 👉 Acting as the first filter before issues reach founders or developers 👉 Feeding high-quality insights back to product and leadership 👉 Helping shape how customer support should operate as we grow

Who This Role Is Perfect For You will thrive in this role if you: 👉 Have intermediate accounting knowledge including cash flow, P&Ls, and business finances 👉 Are confident solving problems independently 👉 Have experience in customer support, customer success, or operations 👉 Are comfortable working with business owners and financial professionals 👉 Have strong CRM experience and care deeply about organisation and follow-through 👉 Are confident using AI tools, video, and modern support workflows 👉 Want to grow with a fast-moving company

This Is Not the Right Role If You 👉 Prefer to escalate issues quickly rather than investigate first 👉 Need heavy direction to make decisions 👉 Want a slow-paced or highly predictable environment 👉 Dislike ambiguity or rapid growth 👉 Want a narrow role with no evolution over time

Growth & Career Path This is not a junior support role.

As Hello Cashflow scales, the right person is likely to: 👉 Help design and lead the support function 👉 Take ownership of broader customer operations 👉 Move into leadership roles across CX, operations, or product strategy

How to Apply Instead of a long cover letter, please send: 👉 Why this role excites you 👉 Your experience resolving customer issues independently 👉 Your experience with accounting concepts or financial tools 👉 Any experience using AI, video, or screencasts in support

Include your CV and email Jonny Wilson (CEO) at: jonny@hellocashflow.com