Our Team


Howard Oliver – Founder and CEO

Expertise: Technology Marketing Strategist, PR, Content Marketing, Business Development

Howard Oliver is the founder and CEO of What If What Next™. What If What Next™ is a boutique agency that offers PR and Inbound Marketing services to technology companies: cloud computing, IoT, data centers, software, hardware, consulting and beyond.

Howard has been a technology visionary, entrepreneur, strategist, writer, content builder, thought leader, PR maven, and business development executive. He provides leadership in the application of Agile and Lean project management methodologies. Clients recognise him as a result driven, highly creative and disciplined thinker.

Howard is a RIC Center Advisor. As the gateway to the Ontario Network of Entrepreneurs, RIC Centre is go-to-place for innovation support in Mississauga, Brampton, & Caledon. He supplies expertise in Technology Marketing, PR and Content Marketing.

Howard holds an MBA from Wilfrid Laurier University and a Bachelor of Commerce degree from McGill University. He is a spiritual seeker, avid sailor, and collector of books. Contact Howard Oliver directly at info (at)  whatifwhatnext (dot) com or 416-568-5254.

Howard is an in-demand speaker and workshop leader at various PR, marketing, and technology events. He is active on social media at http://www.whatifwhatnext.com/blog, @HowardTO , @CloudVentures and whatifwhatnext.tumblr.com/.


Dan Miles – Senior Government Relations 

Dan Miles is a senior executive with extensive experience in strategic communications and government relations. He has had repeated success developing and executing targeted communications, marketing and issues management plans at three levels of government and the university sector.

Having held senior positions with the federal Minister of Finance, federal Minister of Labour, the Ontario Minister of Energy, the Ontario Minister of Community and Social Services and the Chairman and CEO of York Region, Dan has an acute understanding of the government decision making process, including the development of policy and federal and provincial budgets.

Dan also held senior positions at the University of Ontario Institute of Technology (UOIT) in Oshawa and Trent University in Peterborough. He was also a journalist for CTV in the Queen’s Park Press Gallery in Toronto.


donDon Sheppard P.Eng. – Senior Cloud Computing and Cyber Security Consultant

Don Sheppard is a consultant and writer based in Toronto, Ontario. Don has been an information and communications technology engineer, manager and consultant for more than thirty-five years.  Don’s experience has been varied; it includes infrastructure planning, IT procurement, technology assessment, project management and training.  Don has authored numerous whitepapers, has developed and presented courses and seminars and has co-written a book.  Currently, Don is an active blogger on emerging technologies for IT World Canada.  Don is also known for his long-term involvement in ISO standards for open systems interconnection, banking and, more recently, cloud computing.


Rachel Professioal ShotRachel Oliver – Social Media and Content Strategist

Rachel is a social media specialist and content strategist with 7 years of experience. She brings a powerful combination of craft and creativity in her content creation and is talented at writing in any style, for any target market or medium. She is our eye to reaching the millennial generation. She is a social media expert and content strategist. She has worked with clients from a plethora of industries, each time developing a compelling editorial voice for the brand and creating dynamic conversations and campaigns through optimal social media platforms. Working for What If What Next, she played a significant part in creating Web Voyaging™, a strategy generating content through tailored outreach on multiple platforms to drive engagement and leads to client websites and social media platforms. She has a proven track record of working hard on behalf of clients to achieve measurable and meaningful results. In an effort to demonstrate that cats are, in fact, better than dogs, she vigorously participates in posting adorable photos of her cat on Facebook and Instagram. Rachel is a graduate of York University with an Honours degree in Communications Studies.


Farla Klaiman – Editorial Consultant


With her finely attuned eye and ear for language, Farla moves the reader of your copy from “comma coma” to curiosity and engagement. She has experience in content editing, copy editing, and proofreading in a variety of genres, from academic and health care to marketing and memoirs. Farla holds a bachelor’s degree in sociology from McGill University, a master’s degree in speech/language pathology from Dalhousie University, and a certificate in editing from George Brown College. She can explain the difference between “it’s” and “its” in a way you can understand, appreciates the merits of cats and dogs alike, and seeks simplicity and joy in language and life.

To find out more about our work contact us at: 416-568-5254 or info@whatifwhatnext.com.