Ryan Flanagan, Finance Expert in Melbourne, Victoria, Australia
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Ryan Flanagan

Verified Expert  in Finance

Customer Experience and Digital Strategy Expert

Melbourne, Victoria, Australia
Toptal Member Since
December 20, 2022

Ryan led the digital strategy at Marriott and Mirvac, overseeing $60 million P&Ls across ANZ. He transitioned into innovation and digital strategy consulting at IBM, advising some of Australia's largest corporates, before taking APAC RGM positions in tech scaleups like Zomato and CloudKitchens, leading product, sales, marketing, and operations teams of 90+. Ryan freelances to provide clients with decades worth of insight into new venture architecture, innovation design, and digital strategy.

Career Highlights

Education Highlights

Certified Web Analyst
University of British Columbia | Online
Graduate Certificate
Cornell University | Online

Certification Highlights

Case Studies

Work Experience

Executive Coach

2022 - PRESENT
Shackleford Executive Coaching
  • Served as a Certified Master Intelligent Leadership Executive Coach utilizing the unique, powerful, and game-changing intelligent leadership (IL).
  • Utilized executive coaching philosophy, process, content, and tools created by John Mattone, former executive coach to the late Steve Jobs and the former CEO of PepsiCo, Roger Enrico.
  • Helped leaders align their inner core values and character to the practical outer core skills needed to successfully meet these disruptive challenges.
Focus areas: Leadership, Executive Coaching, Mentorship & Coaching, Career Coaching

Innovation Consultant

2022 - PRESENT
11 Point 2
  • Oversaw innovation management and idea validation for emergency services and fire tech.
  • Led innovation management and idea validation for member services and travel tech.
  • Provided assistance in building an operating model for innovation management practice.
Focus areas: Upstream Oil & Gas Management, Government Contracting

Director of Strategy | Customer Experience

2022 - 2022
Government of South Australia
  • Created the whole of government CX roadmap, including the feasibility of global best practice solutions, including formulating innovative, big-thinking ideas that leverage emerging technologies;
  • Identified and developed a customer experience strategy and roadmap to 32 transformational digital strategy programs across the South Australian Government.
  • Ensured effective stakeholder engagement, consultation, communication, and collaboration with government agency executives and staff across the public sector to inform the priorities of the customer experience strategy;
Focus areas: Customer Experience, Digital Transformation, Business Strategy

Regional General Manager | APAC

2021 - 2022
  • Managed the APAC profit and loss as a business owner for the region. I designed and executed the APAC growth strategy to ten times the business and maintained healthy margins.
  • Defined and operationalized the playbook to localize, refine and grow individual APAC markets, including the operating model, pricing, channel relations, and product to increase market share.
  • Led record growth months in June and July for Australia, South Korea, Singapore, and Malaysia in GMV through the platform and maintained scalable unit economics payback period, LTV/CAC.
Focus areas: Sales Growth, Gross Margins, Cross-functional Team Leadership, Business Strategy, Growth Strategy


2020 - 2021
  • Led and formed the partnership program with a range of international value-added resellers, OEMs, POS providers and integration partners in the US, resulting in two large multi-year $200,000+ ARR clients.
  • Built a CRM, opportunity pipeline, and market-led growth plan, including creating sales collateral, sales enablement kits, sequential outreach, and metrics associated with sales velocity resulting in an eleven percent increase in MRR.
  • Developed revenue share partnership agreements with Shopify, clutch, Bazaarvoice, YotPo, magneto, NRC, WooCommerce, and value-added resellers in the US to create additional sales opportunities at the value of $120,000+ in MRR.
Focus areas: Retail Technology, Cannabis, Point of Sale, Sales Growth, SaaS, Pitch Decks, Business Strategy, Growth Strategy


2019 - 2020
  • Created investor deck, approached investors, ran presentations, and developed the roadmap and business model of a first-to-market D2C application for a seed investment of $1 million.
  • Developed a world-first audio-visual short-form mobile video review platform - created gamification to elicit higher volumes amongst review categories and launched product MVP to 300 early adopters with growth rates of nine percent.
  • Designed the revenue goals, OPEX budget, and profit and loss controls while owning organizational governance and risk management to ensure statutory compliance and full accountability to equity and note holders while hiring a team of ten.
Focus areas: Seed Fundraising, Team Management, New Products, Sales, Marketing, Human Resources (HR), Statutory Returns, Statutory Reporting, Gross Margins, Early-stage Startups, Business Strategy, Growth Strategy

General Manager ANZ

2018 - 2019
  • Restructured the operating model to re-set the business for cost-efficient double-digit revenue growth while navigating the complexities of a complex market through new product launches and a revenue increase of 23 percent quarter on quarter.
  • Implemented an EVP to improve behaviors and performance outcomes. I adjusted development milestones, training programs, and compensation adjustments for key roles leading to a ten times increase in satisfaction ratings.
  • Created the business case, worked with technology teams, and made the go-to-market, pricing, and sales enablement to launch three new products, resulting in a three times diversification of revenue streams at four times contribution margin increase.
Focus areas: Teams, Revenue Strategy, Costs, New Product Development, Statutory Reporting, Human Capital Strategy, Business Strategy, Growth Strategy

Managing Consultant

2017 - 2018
  • Worked on defining the customer journey and experience for one of ANZ's largest telco's resulting in cost savings across channel delivery and increased revenue generation from digital operating model design.
  • Led a team of five digital strategy consultants to redefine the citizen offering for Australia's most significant state government, resulting in seamless service delivery to citizens and increasing NPS by six percent.
  • Built the capability and technology roadmap for a big four institutional bank to build innovation capability across customer offerings in transactional banking and personal loan book to lower cost-to-income ratio.
Focus areas: Customer Experience Design, Innovation Strategy, Target Operating Models, Capability Build-out, Business Model Canvas, Business Strategy

Head of Digital Transformation

2013 - 2017
  • Built channel mix, channel profitability, and volume trends and mix analysis. I then created a capability and delivery model and targeted the business's to-be state, culminating in a fully costed business case.
  • Led the entire technology digital transformation of a complex $350 million franchise business with 174 locations across digital technology channels and operating models.
  • Programmed a fifteen percent increase in gross revenue and a bottom line cost reduction measured in +$1 million over 12 efficiency dividends from optimizing workflows and establishing digital practices.
Focus areas: Digital Transformation Program Management, Customer Experience, Financial Modeling, Business Technology, CRM Systems, Channel Management, Sales & Channel Enablement, Digital Transformation, Business Strategy

Director of Digital

2009 - 2013
Mirvac Group
  • Built a digital operating model within the business to support digital channel growth. Including creating a budget-neutral self-funding paid search program shifting marketing to a transaction cost.
  • Developed both volume and conversion rate increases which enhanced gross revenues sourced through the direct channel up to twenty-two percent MoM due to enhancements in search, resourcing, and content across web and mobile assets.
  • Created the first transaction-based search program in the country. This shifted the cost of revenue from an SG&A expense to a transaction cost, grew share voice by three hundred percent, and funding by eighty percent YOY.
Focus areas: Customer Experience Design, Digital Strategy, Digital Marketing Strategy, User Testing, Website Audits, Web Search

Director of Digital ANZ

2005 - 2009
  • Defined a new capability model that mapped the churn rates of existing customers and costed the LTV/CAC of acquiring customers to a unit economics level. I then build a new target operating model based on loyalty unit economics.
  • Increased the online channel revenues by twenty-seven percent, achieving the over-performing benchmark for three consecutive years across 26 websites and 700 pages of eCommerce content.
  • Built a predictive model that reduced loyalty churn by eleven percent in a business with a $30 million EBITDA and an analytics warning and workflow intervention which measured per member contribution margin and trigger points for sales.
Focus areas: Digital Channels, Sales & Channel Enablement, Business Strategy
2012 - 2013

Master of Business Administration (MBA) in General Studies

University of Melbourne - Melbourne, Australia

2011 - 2011

Certified Web Analyst in Analytics

University of British Columbia | Online - Vancouver, British Columbia

2009 - 2009

Graduate Certificate in Advertising and Marketing

Cornell University | Online - Ithaca, New York

1998 - 1998

Senior Year in Economics

Old Dominion University - Norfolk, VA

1996 - 1998

Bachelor's Degree in International Business

Flinders University of South Australia - Adelaide, South Australia


YBF Startup Immersion Program



Blockchain Essentials



Cognitive Practioner



Enterprise Design Thinking



Programme Management



Statutory Returns, Seed Fundraising, Blockchain, Financial Modeling

Industry Expertise

Cannabis, Early-stage Startups


Design Thinking, Innovation Strategy, Startup Consulting, Service Design, Customer Experience, Digital Transformation, Gross Margins, Team Building, Retail Technology, Team Management, Marketing, Statutory Reporting, Foodtech, Teams, Customer Experience Design, Business Model Canvas, Digital Transformation Program Management, Channel Management, Digital Strategy, Digital Marketing Strategy, Website Audits, Web Search, SaaS, Pitch Decks, Business Strategy, Growth Strategy, Organizational Design, Program Management, Point of Sale, Revenue Strategy, Costs, Sales & Channel Enablement, User Testing, Digital Channels, Microsoft, Entrepreneurship, Innovation, Web Marketing, Google SEO, Web Analytics, Artificial Intelligence (AI), Sales Growth, Cross-functional Team Leadership, New Products, Sales, Human Resources (HR), New Product Development, Human Capital Strategy, Target Operating Models, Capability Build-out, Business Technology, CRM Systems, Upstream Oil & Gas Management, Government Contracting, Leadership, Executive Coaching, Mentorship & Coaching, Career Coaching

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