Business Development Representative (BDR)

What if your first real sales role wasn’t just another SDR grind, but a chance to help define an entirely new category in AI?

Companies are scrambling to figure out how to show up in AI recommendations before prospects even visit their website. Yolando is building the leading platform that helps companies do exactly that, and win in the era of AI search.

We’re growing quickly and actively looking for a driven early-career seller who wants to learn fast, earn big, and be part of something genuinely important.

If you’re ambitious, competitive, curious about AI, and want to build a career in tech sales, this is the kind of opportunity that rarely comes along twice.

Why This Role Is Exciting:

Yolando recently launched commercially after raising $8.5M USD in funding from Drive Capital, one of the most respected venture firms backing breakout companies.

The platform helps companies understand how they appear in AI-generated answers from tools like ChatGPT, Claude, Perplexity, and Gemini, and how to improve that visibility.

In this role, you’ll work directly side-by-side with the founders, helping turn founder-led sales into a scalable engine.

You’ll learn:

• How startup sales really works

• How to identify high-value opportunities

• How to build pipeline from scratch

• How AI is reshaping marketing and search

For someone early in their career, this is a masterclass in modern SaaS sales.

This is a high-impact revenue role where performance is rewarded.

Base salary:
$60,000 – $80,000 CAD

On-Target Earnings:
$100,000 – $120,000+ CAD

Uncapped commission:
The more pipeline you generate, the more you earn.

Our team is currently 15 people in Toronto, which means:

• Your work will have visible impact

• You’ll gain real ownership

• You’ll learn faster than you would in a large company

• You’ll build skills that will be incredibly valuable as AI reshapes marketing

And yes, there’s equity!  If Yolando becomes the category leader we believe it will be, you’ll be glad you joined early.

You’ll be responsible for building the pipeline that fuels the company’s growth.

That includes outbound prospecting through cold email, LinkedIn outreach, cold calling, and multi-touch sequences that cut through the noise and actually get replies.

You’ll research target accounts to identify the right buyers, including CMOs, marketing leaders, SEO heads, and growth teams, while understanding their competitive landscape.

You’ll craft personalized outreach using Yolando’s own competitive intelligence platform, showing prospects where they’re losing visibility in AI search.

You’ll generate pipeline by booking qualified demos and surfacing insights about what messaging works.

This role works closely with Matt (CEO) to test messaging, refine targeting, and improve the overall sales motion. As the company grows, you’ll also represent Yolando at industry events, meetups, and networking opportunities.

Must-Have Experience

• 1+ year experience in BDR, SDR, or outbound sales

• Experience with cold outreach (email, LinkedIn, or calls)

• Comfortable using tools like Sales Navigator, Apollo, HubSpot, or Salesforce

• Excellent written communication

• Competitive mindset and strong work ethic

• Genuine interest in AI, marketing technology, and startups

Bonus Points If You Have

• Experience selling to marketing or growth teams

• Familiarity with SEO or AI search

• Startup experience where things moved fast

You’ll probably love this role if you want to build a career in tech sales, enjoy figuring things out and moving fast, and have a strong competitive drive.

People who thrive here are curious about AI and how technology is changing business, and they’re excited by the idea of being early to something big.

Before a prospect visits a website or books a demo, they increasingly ask AI tools like ChatGPT who they should trust.

If a brand isn’t recommended in those answers, it may never even get considered.

Yolando helps companies shape those answers and win the conversation before it begins.

The category is just emerging — which means the people who get involved early will build the most valuable expertise in the space.

If you want to be early to the next wave of marketing technology…

This is your chance.

Send us:

• Your resume

• A short note explaining why this role interests you

• A sample cold email you’d send to a VP of Marketing at a B2B SaaS company

Email: [email protected]

We move quickly. If you’re a strong fit, you’ll hear back within 48 hours.