In cities like Toronto, New York, Vancouver, and Austin, tech companies are growing fast, but many are still getting one critical hire wrong: the Sales Executive. Whether you’re a SaaS startup or a cloud infrastructure firm, your ability to scale hinges on hiring Sales Executives who can sell into complex organizations and bring in real, repeatable revenue. Yet time and time again, companies stall out after raising capital because they rushed the hiring process or hired the wrong profile altogether.
At Quota Crushers Agency, we’ve interviewed thousands of B2B Sales Executives across North America, and we consistently see tech companies making the same mistakes. In this article, we’ll unpack what goes wrong, what top candidates actually look for, and how to attract the Sales Executives who close.
Why do so many early-stage tech companies struggle to hire good Sales Executives?
Because they treat the hire like a Swiss Army knife instead of a specialist. Many founders try to hire someone who can generate leads, close six-figure deals, build decks, and train the SDRs, then wonder why the pipeline doesn’t move. The best Sales Executives are not generalists. They are closers with a playbook. They want to know exactly what kind of sales motion the company is running, who the buyer is, and whether the product is truly ready for scale.
What are the red flags for Sales Executives during the interview process?
Top Sales Executives don’t just listen to the pitch. They study your signals. If your compensation plan is vague, your quota is unrealistic, or your GTM team is disorganized, they will walk. In high-demand markets like California and Texas, candidates receive multiple offers and can be selective. Common turnoffs include unclear territory structures, lack of SDR support, long approval cycles, and inconsistent messaging from leadership.
What do top Sales Executives want in a tech company?
They want three things: clarity, confidence, and credibility. They want clarity on quota, compensation, and expectations. Confidence in leadership and product-market fit. Credibility in the form of real customers, strong retention metrics, or a clear go-to-market strategy. If you can’t articulate why now is the right time to join, they will not be convinced.
What kinds of questions do Sales Executives ask during interviews?
These are real questions we get from top-tier candidates across Canada and the United States: How many AEs hit quota last year? What’s the average deal size and cycle length? Who are your best customers and why did they choose you? How much support is provided in terms of SDRs, sales enablement, or marketing? What percentage of the comp plan is tied to upsells or renewals? If your hiring manager can’t answer these clearly, your offer likely won’t land.
What is the best way to structure the hiring process?
Keep it to three rounds. The first interview should qualify technical selling experience and motivation. The second should test deal strategy and industry knowledge, ideally with a VP or sales leader. The final round should include a clear case study or role play, with a decision made within 72 hours. Sales Executives are fast movers. If you want to hire one, you have to operate on their schedule, not yours.
What locations are most competitive for tech sales talent right now?
In Canada, Toronto and Vancouver are highly competitive for SaaS and cloud talent. In the United States, top tech sales activity is happening in New York, Austin, San Francisco, Los Angeles, and Miami. These cities are filled with funded startups. This means your hiring process and employer brand must stand out. You’re not just competing on salary. You’re competing on vision and execution.
How should comp plans be structured for Sales Executives in tech?
OTE should be realistic and achievable. Base salaries vary, but most mid-market to enterprise tech companies are offering base salaries between 90K and 130K in USD or CAD, with OTE targets of 180K to 260K. Top performers expect accelerators, territory protection, and transparent KPIs. If you’re not offering these, do not be surprised when your competitors start poaching your team.
What is the cost of hiring the wrong Sales Executive?
For early-stage companies, it can mean six to twelve months of lost pipeline, missed revenue targets, and reputational damage in your category. Worse, a bad hire often leaves behind a messy CRM, damaged relationships with prospects, and a demoralized team. Hiring right the first time is not a luxury. It is a requirement.
What industries are hiring tech Sales Executives right now?
Outside of traditional SaaS, there is strong demand for sales talent in cybersecurity, fintech, logistics tech, AI, and enterprise infrastructure. If your company plays in one of these sectors, expect fierce competition for experienced closers who understand the space.
Final Thoughts
Hiring a Sales Executive for your tech company is not just another hire. It is the person who will shape how the market sees you, how fast your pipeline grows, and how often you win against competitors. If you’re not attracting the right candidates or losing them mid-process, your entire growth plan is at risk. Quota Crushers Agency specializes in recruiting top-performing Sales Executives across North America’s tech landscape. We work with companies in Toronto, New York, Austin, and beyond to help them secure the talent that delivers real revenue.
