David Grossman

Founder & Chief Executive Officer - Lessn | B2B Payments & AP Automation | Fintech Innovator

Greater Sydney Area

About

I’ve spent my career at the intersection of finance, technology, and entrepreneurship, driven by a simple belief: business should be smarter, more connected, and built on trust. My journey has taken me from corporate finance and banking to fintech startups, where I’ve focused on solving real problems for businesses. Along the way, I’ve learned a few things that guide everything I do: 1. Technology creates opportunity, but only when it solves real challenges. 2. Relationships drive business because trust moves faster than transactions. 3. People matter more than ideas because the right team can turn any idea into a success. That mindset has shaped how I build, lead, and innovate. Now, with Lessn, we’re making business payments work better, helping companies automate, optimise cash flow, and turn expenses into financial advantages.

Experience

  • Founder & Chief Executive Officer at Lessn
    Feb 2025 - Present · 1 yr 5 mos

    Lessn is a smarter, faster, more rewarding way for SMBs and their finance teams to centralise, manage and pay invoices - Save time, reduce errors and complete bulk actions Automate payments with auto-reconciliation via accounting integrations - Maximise rewards Pay any expense with any funding method (Amex, V/M) - Cash flow control and orchestration Split payments, extend terms, unlock early payment discounts - Secure digital wallet, audit trail and permissions Manage payment methods, user permissions and payment history in one place

  • Partnerships, Advisor & Team Builder at Sydney Transport Group (STG)
    2020 - Present · 6 yrs 6 mos

    As an executive advisor, I assist win large tenders, assemble and build teams around projects, originate partnerships and identify technologies which progress the growth of the group. Most notable achievement: Won FIFA Women’s World Cup Tender across Australia and New Zealand for the movement of talent and media teams during the 2023 World Cup

  • Principal at Pemrose Group
    Aug 2018 - Present · 7 yrs 11 mos

    Personal Management Company and investment vehicle for venture capital, investments and shareholdings.

  • Evangelist at Photon Energy Group
    Apr 2018 - Mar 2020 · 2 yrs

    Origination of commercial/industrial solar contracts and solar farms

  • Partner at Opportunity Capital
    Jan 2018 - Jan 2020 · 2 yrs 1 mo

    Origination of the group's founding investment in Koh.com and other early stage growth technology companies. www.oppcap.com.au