Introducing our newest portfolio company, MilestonePay!

Hannah Parton-Cyr
Black Sheep Capital
6 min readJun 1, 2021

COVID has had a considerable, meaningful and lasting impact on the world — particularly in how we do business and how we interact. According to the ABS, after more than a year of COVID, approximately 41% of workers are working from home a minimum of once per week[1]. These changes post-COVID have only amplified trends in recent years in the space of digital natives and freelancing. As the number of those seeking remote work increases, careers for digital natives who can work from anywhere — like software developers or graphic designers — has continued to boom. In the US, the share of freelance workers increased eight percentage points in 2020 to account for over a third of all workers[2]. And this trend is likely to have staying power; 60% of post-COVID freelancers on Upwork now say that there is no amount of money that would convince them to take a traditional job[2].

Digital native agencies have also had to make changes to the way that they do business, adapting how they engage and meet with their clients and project stakeholders. Whereas traditional agency projects might have kicked off with in-person meetings and brainstorms, the industry has been forced to accelerate a shift to flexibility post-COVID. Agility in this space is key, but digital agencies still rely on systems and processes for engaging with their clients that span from emails to texts and to invoices across various project stakeholders.

Yet, with all the macro changes happening in the world of digital natives and agencies, some things never change. There are still serious pain points in the industry which remain the same, including:

  • Combating feast vs famine when it comes to cash flow;
  • The difficulty of getting payment post completion of the work in a timely fashion — and the risk that you might not get paid at all. According to a comprehensive survey of freelancers in APAC, over half of all freelancers in struggle to manage their cash flow, with 43% struggling with late paying clients and long payment cycles[3].
  • Client expectations differing from the scope of works agreed upon, often aggravated by the lack of a central system to communicate and share project updates.

Our team believes that we have found the right company and right founding team working to solve these problems, and that this opportunity will only get bigger as remote working opportunities and remote client engagements become a permanent fixture of digital native work.

Introducing MilestonePay

MilestonePay is the only contract generation and payments platform that specifically addresses the problems faced by digital agencies and freelancers in managing contract scope, payments and project overheads. Through MilestonePay, users are able to manage their invoicing, contracts and forms, clients and payments, allowing them to focus more time on doing what they love and not stressing the admin.

This is how the platform works…

MilestonePay allows you to build out contracts and split projects into achievable milestones, which consist of deliverables associated with each milestone and an associated cost. In engaging with the platform, the customer must pay for each milestone upfront to enable the supplier to begin work. Those funds are then held in escrow and released upon approval from the client that the work was done according to the pre-determined contract deliverables. This ensures that there is alignment between the customer and supplier on expectations, making the lives of their agencies and freelancers much smoother.

A screenshot of the MilestonePay platform.

Beyond contracts, MilestonePay enables its users to see the live statuses of their proposals and contracts. You are able to save contract templates, making it easy for you to reuse templates with onboarding new clients. Overall, MilestonePay is building the framework and tools for gig economy workers to be empowered to manage their businesses.

Why are we so excited about this company?

One of the first steps when evaluating a start-up is grasping the problem that the team is trying to solve for, and whether you believe the problem statement is deep enough to warrant a closer look. After meeting the founders of MilestonePay, Ryan and James, we knew that the team was solving a very deep and personal issue. With over 30 years of software development experience between the two of them, both Ryan and James had struggled with non-payment in the past freelancing for clients both in Australia and abroad. They knew that so many freelancers faced hurdles in getting started and knowing how to establish themselves and their processes in order to get their businesses up and running.

The founders

The founders of MilestonePay, Ryan Handby and James Claridge, have weathered the storms of both agency and freelance contracting. The guys have known each other since their time at ROLLER Software and have a chemistry which is hard to match.

Co-Founders Ryan Handby (left) and James Claridge (right)

Ryan Handby, CEO: Ryan is a software developer, with experience working as a Programmer across four organisations including ROLLER, where he met James. While at ROLLER, Ryan led the machine learning, payment integrations and ticketing platform teams with a team of technical staff under him. In a prior life, Ryan was a professional gamer, ranked globally for BF2142, World of Warcraft, StarCraft and Hearthstone. When he’s not working on MilestonePay, he enjoys spending time with his border collies.

James Claridge, CPO: James is also a full stack engineer with a diverse experience across various digital payment mediums, Ex Head of Product at ROLLER, Technical Project Manager at Balance Internet and CTO of Flux Agency. James is a serial entrepreneur; he has built numerous ecommerce SaaS products which currently serve millions of visitors a day with an emphasis on performant speed solutions. Although James is never really off duty, he spends his spare time delving into the biochemistry of marine ecosystems or consuming coffee with a religious fervour at one of his regular haunts.

We’ve really enjoyed getting to know both Ryan and James and can’t wait to continue working with them.

The progress

Since we first met MilestonePay back in August 2020 for the first time, we have seen the company grow leaps and bounds. James has been relentlessly dedicated to rolling out new features on their tech roadmap, while Ryan has been leading the charge on acquiring new customers and focussing on strategy. Point blank: these guys execute. And their focus on building the product and refining their value proposition has translated into some great early traction for MilestonePay.

Since our conversations first began, the team has onboarded over 150 clients to the platform and has had over AU$180k payments processed through MilestonePay. The team recently completed the Startmate ’21 accelerator program in April this year and are continuing to build on the knowledge and guidance they received from the program.

We’re thrilled to be working with MilestonePay… and you could be too!

The team is on the hunt for 10 lucky digital agencies to be given one year free of pro-MilestonePay. If you want to fix the amount of disparate tooling in your agency and make it all work together seamlessly, then this is a rare opportunity to be part of the roadmap of the team solving that problem for you. These pro-customers will get endless access to MilestonePay’s developers and the insider scoop on MilestonePay’s new features — all in exchange for them letting the team get closer to their business and ensure they are building exactly what makes digital agencies successful.

Shoot an email to hello@milestonepay.com if you are interested in becoming one of the lucky 10.

[1] https://www.abs.gov.au/media-centre/media-releases/year-covid-19-and-australians-work-home-more

[2] https://www.npr.org/2020/09/16/912744566/jobs-in-the-pandemic-more-are-freelance-and-may-stay-that-way-forever

[3] https://freelancejungle.com.au/wp-content/uploads/2019/12/FJ-Survey-2019-FINAL.pdf

--

--

Hannah Parton-Cyr
Black Sheep Capital

Retired chemical engineer. Venture analyst at Black Sheep Capital.