Matt‘s ’Why’ and Point of View

So many businesses struggle to generate enough new sales to take their growth to the next level…and it doesn’t have to be this way.

Throughout my career, first as an inside sales, new business sales, sales leader, executive and finally as consultant and advisor, I’ve seen the same issues at nearly every company I’ve worked at and consulted with, small or large.

Good human beings, new and experienced in business and sales, hard working, motivated and wanting to succeed for themselves, their families, their company and their customers – fail to reach the next stage of their growth and simply repeat the performance of the year before.

This happens for 4 reasons:

1.   The experience, skill and blind spots of the CEO/Founder:

  • A technical or subject matter expert without a sales background who doesn’t know how to scale for growth, or understand and execute the appropriate customer centric go-to-market model for their business. They are reliant on a sales leader who may not have the knowledge and skills to take them to the next level, but is always promising results are just around the corner.
  • An executive with a track record of managing companies with mature products and offerings to existing customers, they lack experience of how to arm the sales force with a new mindset, messaging and skills to capture new markets and new customers.
  • They’ve tapped out their professional network from past lives for growth and haven’t transferred knowledge effectively to new sales hires or replaced/removed themselves as top sales person, so they become the bottleneck and micro-manager to growth. They typically make poor sales hiring decisions or are unable to attract top sales talent.

2.   Sales Leaders are hired who don’t have experience of scaling to the next stage of growth, or have come from a large enterprise and have never worked in a smaller company with constrained resources. Process and activity are the levers they pull on, without giving due emphasis to go-to-market strategy and ‘how’ their sales people are prospecting and selling. How you sell is more important than what you sell. Many sales leaders cannot model the behavior and skills that they expect and demand from their sales people – leadership dysfunction at its highest.

3.   Sales on-boarding is back to front. It focuses on transferring product and internal knowledge to sales and is all about you -your company, your product and why you’re the best. All necessary. And, it should be all about your customer – the value, outcomes and results that they can expect as a result of working with you. It usually isn’t – and that’s why most sales people struggle to discover and communicate customer value and outcomes. This shows up as lots of meetings and proposals, long sales cycles and low win rates.

4.   Most inside sales organization focus their prospecting efforts at the wrong level and role – mid ranking executives motivated by status quo…”who can’t say yes but can say no.” Sales is about introducing change. Change is usually driven by the C suite. Many sales people – and some sales leaders – will admit they struggle to get access to senior decision-making executives at Must Win accounts. The Mindset and Skills to reach out effectively to senior executives are often assumed to be in place and sales reps don’t want their leaders to know they need help. Sales organizations believe this skill is “magically” developed in-house by osmosis, or that they are already getting these skills by employing highly experienced sales people. This shows up as lots of prospecting activity for very few meetings, “no shows” to scheduled meetings, and lack of quality and quantity of opportunities in the pipeline.

I’ve spent my entire career working to address these challenges so that Executives, Sales Leaders and Sales People don’t have to experience the frustration that I went through in my roles. Put good people in a bad system and the people will fail or leave. The way most sales organizations operate sets good people up for hard work and mediocre performance at best, failure at worst. It’s such a shame…and doesn’t have to be this way.

My clients say that my advice helps them get clarity and immediate results for them, their Sales Leaders and Sales People. Consistently.


Matt Conway has an immediate and positive impact on the companies that engage him and the individuals who meet him – on professional and personal levels.

Matt’s background in new business sales, sales leadership, executive leadership, go-to-market strategy and B2B executive copywriting, coupled with his ability to ‘lead from the front’—driving dramatic tactical results—makes him both a valued advisor to executives and a respected mentor and coach to sales people.

Prior to founding his consulting, advisory, mentoring, coaching, copywriting and speaking practice, Matt spearheaded the growth of various startups, professional services, consulting and multinational firms including Franklin Covey’s Sales Performance Practice, a Microsoft participated company, Nokia, the Chasm Group’s UK partner and Michael Page amongst others. Executive responsibilities included launching new concepts/countries, sales and marketing, alliances, industry initiatives, regional roll outs, business planning and restructuring.

Matt is ‘Swenglish’ – half Swedish, half English and has had a wealth of international experience having lived and worked in the Gambia, Nepal, Bangladesh, Indonesia, Sweden, UK , Canada and the USA. Matt resides in Newmarket, Ontario, Canada. He is married to his wonderful and beautiful wife Lindsay – and has 3 great kids aged 17, 15 and 10 (they’re young in this picture).

Matt has a B.A. Hons in International Development Studies from the University of Kent, Canterbury, United Kingdom.

In his spare time, Matt enjoys the great Canadian outdoors hiking, cross country skiing, camping, fishing, personal development (Matthew is a Certified NLP Coach), squash, training German Shorthaired Pointers & Retrievers and cooking…particularly BBQ.