Adventures in Sales: Getting Started as a 28-Year-Old Sales Newbie

young woman working at computer with coffee cup and headset phone

I’m pleased to introduce you to Tegan Samija. With a series of posts, she’s going to share with us, in real-time, how she navigates learning to sell … everything from picking up the phone, speaking with potential clients and booking meetings. I’m joining her on this journey as her occasional coach and I’m really pleased that she’s agreed to write about the experience. 

Tegan Samija
Tegan Samija

‘I work in sales’ is something I thought I’d never say! But here I am, 28 years old and jumping into sales as a part-time sales development rep with a learning and development company.

It’s not that I’ve had anything against sales up until this point; it’s just been part of a distant world of quotas, pipelines, and commissions, and not one I thought I’d be entering anytime soon.

So how did I end up here? With a background in marketing, startups, and social enterprise development, last year I started freelance writing in the tech space. Freelancing has served me well; I’m currently writing this article from Tokyo and spent the last several months working from Vietnam, Malaysia, and Bali.

However, you can’t get far in freelancing without some type of sales, and my main method for finding clients was sending out cold emails. Far from feeling ‘icky’, I actually enjoyed the rhythm of identifying companies, pitching, and following up.

So when I connected (over a cold email, of course) with a prospect looking for freelance sales work, I was intrigued. As a global Learning and Development company, they designed training programs for top corporations and non-governmental organizations, but they didn’t have a sales team yet.

Of course, this meant I’d be a sales department of one. I was excited about the opportunity to design their sales processes and create a simple, effective system for client acquisition in North America and beyond.

Just one small problem – I didn’t have a formal sales background and wasn’t convinced the ‘make it up as I go’ approach I used in my own business would cut it! 

Cue the first person who came to mind when I think of sales and cold calling – Mary Jane! Having attended one of her workshops a few years before, I’d been impressed by Mary Jane’s story of how she used sales to successfully grow her first business, and by her practical approach to sales focused on buyer psychology. It was time to call The Phone Lady.

Fortunately, Mary Jane agreed to help me out, and I’m now a couple of weeks into my new role. Some of my favourite learnings so far include:

    1. Sales is problem-solving. Selling becomes a lot more interesting when see your job as helping prospects solve a real problem. This means listening more than you talk and doing some research before jumping on a call so you can be informed about their challenges.
    2. People buy from people they like and trust. This might sound like an obvious one, but I think it’s a great reminder not to do things like send spammy, generic emails or disrespect people’s time. People will want to buy from you if they trust you’ll put their company’s best interests above making a sale if it’s not a good fit.
    3. Persistence is key. I’ve learned it can take 14+ touchpoints just to book a meeting. And Mary Jane says regularly, “Silence doesn’t mean no!” And yes, it’s possible to continue reaching out in a genuinely helpful way so people actually appreciate your persistence.

These takeaways are pretty general, but they’re some principles that are getting me excited about the world of sales! 

So far, I’ve had a busy few weeks learning about my new team’s service offerings, attending some of our training workshops to experience them firsthand, and researching our target customers. Next, it’s time to write a script and pick up the phone … stay tuned to find out how this millennial does with her first-ever cold calls!

Closing a sale is the natural outcome of inspiring great conversations and listening intently to our potential customers.

This natural approach still involves a process – a plan that moves potential customers through a journey of discovery with you. So ... what's your process? And am I the right sales coach for you? Let's find out.

5 thoughts on “Adventures in Sales: Getting Started as a 28-Year-Old Sales Newbie”

    • Tegan, your post is so genuine. It was a delight to receive and several folks have either called or sent email thanks us for putting together this series. Keep them coming!

    • Thanks for your comment, April. I’ll be sharing it with Tegan. And … part two of her story will be available on Sunday evening. I am so pleased that she’s sharing with us as well. Very valuable.


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What's The Phone Lady doing?


  • Remote learning experiences + one-on-one coaching for women entrepreneurs (More info about this three-year program here.)
  • Team and individual coaching with a national moving company to refine their sales process
  • Remote half-day training for provincial tourism representatives
  • Remote seven-part sales training program for US-based SaaS
  • Remote webinar on accounts receivable communication for industrial-services company
  • Remote webinar on validation to college students in entrepreneur program
  • In-person workshop on job search skills for women in the trades
  • Remote half-day webinar on written correspondence to customers

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