Leadership

Let’s Fix Startup Board Meetings: 5 Sections To Flow

By | Leadership, Startups, Strategy | No Comments

Few things can shatter a founder’s confidence quicker than a poorly managed board meeting.

At best…

… you’ll get glossed over stares and “checked out” investors who secretly hate you for wasting their time.

At worst…

… you’ll accidentally knock over the first domino in getting kicked out of your own company.

Pay special attention to Step #4 in this week’s video to make sure that never happens. Read More

6 Characteristics of Successful SaaS Salespeople

By | Leadership, Sales, Startups | 8 Comments

All SaaS companies need sales people.

Even products like Dropbox & Slack have sales teams.

If you look at the Montclare SaaS 250 list, they all have sales teams.

So why do startups push off making this hire for so long?

It’s usually because they don’t know what to look for and are scared that a new fancy pants sales person wouldn’t close enough deals to cover their cost.

A totally legit concern.

But one you need to quickly blast through if you have any serious hopes of scaling. Read More

How To Compensate & Scale Your Startup Sales Team

By | Leadership, Sales, Startups | No Comments

Have you ever been talked into do something you knew was dumb?

*raises hand*

Back when I was scaling my company Spheric Technologies, a friend introduced me to his buddy who did outsourced sales.

Essentially, a quick fix “easy button” for business owners who can’t be bothered to take full control of the lifeblood of their business. Smart right? 😉

His big promise was that he could get me scheduled meetings with qualified buyers for our services…

… so I gave him a try.

The cost was about $5K/month + a $5K setup, so I gave it a try to see if it would move the needle.

My average deal size was $60K, so I figured just one new customer every month would be a huge win. No brainer, right? Read More

The 5 Parts of Every Business

By | Leadership, Startups, Strategy | 2 Comments

Do you remember the first time you had someone buy something from you?

For me it was when I convinced a bunch of bed & breakfast owners in Atlantic Canada to send me cash in the mail to have their property published online.

Still not sure if that was legal.

Suspect cash collection methods aside…

What they didn’t know is that I was a 17 year old kid with no formal “business.” Read More

The Ikea Effect: How To Use a Simple Analogy To Hire Your Next C-Level

By | Leadership, Startups, Strategy | 4 Comments

One of my favourite questions to ask someone is “Who’s the best [CMO/CTO/VP of Sales] you know?”

I don’t care if they already have a job… I just want their name.

Actually, I prefer if they’re already working because it allows me to build a relationship with them without the pressure.

My approach once I have a name is to reach out with a big, real-world challenge that I can get their advice on…

… usually the first contact lasts 15 minutes.

I’m just looking to establish a connection.

From there, I follow up and keep the conversation going and work them through my process for hiring.

But what if you don’t know anyone to ask? Read More

Where to find a code-cranking unicorn (aka CTO)

By | Leadership, Startups, Strategy | One Comment

Steve Jobs (Apple) had Steve Wozniak.
Mark Zuckerberg (Facebook) had Dustin Moskovitz.
Bill Gates (Microsoft) had Paul Allen.

Even though they could all code themselves, the greatest business leaders of our generation, all had a technical co-founder by their side.

Why?

They knew they’d need help building the actual product as their focus shifted to growing the business.

I had the same experience in my companies.

How did they find these people?

How did they convince them to join them in their vision? Read More

Tools For Entrepreneurs: Managing Software Development

By | Leadership, Productivity, Startups | No Comments

In 2001, I got a job I wasn’t qualified for.

I was hired by a big oil company to lead a new project with dozens of developers to build a product that would be used by every employee in the company.

No pressure, right?

On the first day, the hiring manager realized I was in way over my head and pulled me aside to tell me I had 2 weeks to “figure things out”.

Umm… ok?

I had no clue what that meant… but the stakes were clear, and I couldn’t lose this project.

I hadn’t worked in 2 months and if I failed, it meant moving back in with my parents. Read More

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