Sales Director (Toronto)

Location: Toronto, ON (145 Front St E). Hybrid, with regular time in our Toronto office

Employment type: Full-time, permanent

Reports to: CEO

Team: One Account Executive today; you'll hire and lead the team as it grows

Base salary: CAD 100,000 to 150,000 per year, plus commission based on sales results. Commission structure is discussed during interviews.

Start date: As soon as possible

Vacancy: This is a new position, and it is an existing vacancy we are hiring for now.

About Productive Shop

Productive Shop is a Toronto-based B2B marketing agency that works only with SaaS and technology companies, many of them backed by venture capital or private equity. Since 2012, we've helped software companies such as Box, Conga and FireMon build pipeline through search engine optimization (SEO), generative engine optimization (GEO, which gets brands cited in AI assistants like ChatGPT, Perplexity and Gemini), content, paid advertising, website design and development, and AI workflow automation. Most of our clients are mid-market and enterprise companies in the US, in fields like cybersecurity, fintech, data and logistics. We measure every engagement the same way: does it build a reliable forecast, bring the right traffic, engage buyers, convert them into qualified leads and produce revenue?

We also built our own AI platform for marketing teams. Clients use its agents to handle research, content briefs, writing, analytics and trend reports themselves, while our team leads the strategy, account management and consulting. That mix of software and expert services is what you'll be selling.

The opportunity

You'll be our first Sales Director, reporting to our CEO. Until now, sales have been led by the CEO with one Account Executive. Your first job is to sell: build pipeline, run deals and close new business yourself. As you prove what works, you'll hire, train and lead the team that scales it. You'll sell a mix of software and agency services, and help decide how we go to market.

What you'll do

Win new business

• Own the full sales cycle, from prospecting and discovery through proposal, negotiation and close.
• Build pipeline through outbound prospecting, referrals, partners and inbound leads.
• Run consultative sales with marketing leaders (CMOs, VPs of Marketing, heads of growth and SEO) at SaaS and technology companies.
• Carry a new-business sales target set by the CEO.

Build, train and lead the team

• Manage, coach and train our current Account Executive and every sales hire after them.
• Write the sales hiring plan, then recruit and onboard new team members.
• Set clear, measurable goals and hold regular one-on-ones and pipeline reviews.
• As the team grows, define roles, territories and performance expectations with the CEO.

Sell software and services together

• Sell subscriptions to our AI platform alongside agency services, and help prospects choose the right mix.
• Work with our delivery leads to scope services and write proposals and statements of work before anything is sold.
• Price deals to win business while protecting margins.
• Hand signed clients to our account management and delivery teams with everything they need to start well.

Build the sales process

• Design a repeatable sales process, playbooks and qualification criteria.
• Own forecasting, pipeline reporting and CRM accuracy.
• Use conversion and pipeline data to find where deals stall and fix it.

Shape how we go to market

• Work with the CEO on target customers, positioning, pricing and packaging for our AI platform and services.
• Work with marketing on pipeline generation, and bring customer feedback to our product team.
• Represent Productive Shop with prospects and at industry events.

What success looks like

Targets are set with the CEO. In broad terms:

• By 6 months: a documented sales process and a CRM pipeline the team uses every week; a forecast the CEO can rely on; new business closed; your first sales hire made.
• By 12 months: a growing team that is meeting the new-revenue targets set with the CEO.

What you bring

• 2+ years as a Sales Director, or in an equivalent role leading a sales team, including hiring, training and coaching sellers.
• 7+ years of B2B sales, with a strong record in SaaS and of meeting or beating quota.
• Experience building or rebuilding a sales process, team or function.
• Consultative selling on complex deals with several decision-makers.
• Comfort selling both software and services, and explaining how they work together.
• Skill with pipeline management, forecasting and CRM discipline.
• Clear written and spoken communication, including presenting to senior executives.
• A university degree is preferred; equivalent experience is also considered.

Nice to have

• Sales experience in martech, SEO, AI search or content marketing software.
• Experience selling agency or managed marketing services.
• Experience selling to mid-market and enterprise companies in the US.
• Hands-on use of AI tools in your own sales work.
• Experience with sales tools such as HubSpot, Salesforce, Apollo or LinkedIn Sales Navigator.

If you meet most of this but not all of it, apply anyway and tell us what you've done that's relevant.

How we work

We work best in person. Time together in our Toronto office is how we coach, solve problems quickly and build the team, so this role is hybrid, with regular time in the office each week. If you need an accommodation, tell us during the hiring process.

Pay and benefits

• Base salary of CAD 100,000 to 150,000 per year, plus commission based on sales results.
• Group health benefits.
• 3 weeks' paid vacation.
• Paid statutory holidays.

How we hire

1. Application review by our team
2. Short screening call with HR
3. First interview with our CEO by video
4. Final interview and reference checks

Everyone we interview will hear from us about whether we've made a hiring decision within 45 days of their last interview.

Equal opportunity and accommodation

Productive Shop is an equal opportunity employer. We welcome applicants of every background and assess candidates on their skills and experience. Accommodation is available on request at every stage of the hiring process. If you need one, mention it in your application or let us know when we contact you to schedule an interview.