Founding Head of Sales

Hiring tools built by tech-first recruiters who lived the pain.

RisePoint Careers is a Calgary-based B2B hiring solutions company on a mission to make recruitment faster and clearer on both sides of the table. The team builds two products: Spark Enterprise, a recruitment operating system for lean hiring teams with explainable ATS scoring and a Kanban interview workflow, and SparkCareers, a free clarity tool that helps job seekers see how their CV stacks up before they apply.

The founders are tech-first recruiters — they have felt the pain of hiring with bloated, expensive ATS tools, and they have built the platform around the friction, not the other way around. There is early traction. There are paying users. There is a product-market fit hypothesis that needs sales leadership to validate and scale.

100 paying customers. 90 days.

That is the number. Same target, same urgency, harder problem — because this hire owns more than execution. Assume there is no playbook (the thin one that exists, you will rewrite). Assume there is no CRM dialed in, no ICP defined to your standard, no pricing tested, no sequences built. Your job is zero to one.

You hit the number while building the engine that makes the next 100 customers cheaper and faster than the first. Founder sets direction on product. Sales is yours.

Build the engine. While running it.

This is not a pure execution seat. The 90-day target is real, and you will be closing deals yourself — but you are simultaneously building the function that will outlast your first cohort of customers. Both at once.

• Build — sharpen the ICP, build the messaging, define the qualification criteria, set the pricing experiments, stand up the CRM and reporting. The thin playbook that exists is a starting point, not a constraint.
• Sell — run the full cycle against the 100/90 target. Multichannel outreach — phone, LinkedIn, email, warm intros, content — sequenced for the buyer. Demo Spark Enterprise. Close. Repeat.
• Instrument — pipeline metrics, conversion data, win/loss analysis. You know what is working and what is not because you are measuring it, not because you have a hunch.
• Compound — turn early wins into a repeatable playbook. Document what works so the function can scale past you when revenue justifies the next hire.

Decision rights expand with proof. The first 90 days are execution-heavy with strategic input. Once the model is working — pricing, ICP, channel mix — the call increasingly becomes yours.

The traits that matter.

• Track Record
  Seven-plus years in B2B sales
  At least seven years of full-cycle B2B sales experience. Six can work if the experience is genuinely exceptional — standout track record, time at an exceptional org, founding sales seat at a real startup — but not less. You have carried real targets and hit them.
• Zero to One
  You have built sales from scratch
  You have been the first sales hire, or close to it, at least once. You know what it means to walk into a function that does not exist and build it — ICP, sequences, CRM hygiene, pricing tests, the whole stack — while still hitting a number.
• Channel Range
  You sequence channels, you don’t pick one
  Phone, LinkedIn, email, warm intros, content. You bring real fluency across the mix and the judgment to know which to lead with for a given buyer. You pick up the phone when that is what the deal needs.
• Operator Mind
  You think in systems, not just deals
  You can talk a closed-won deal with the founder in the same conversation as conversion-rate diagnostics, sequence optimization, and what a repeatable motion needs to look like. Strategic and tactical, same person, same hour.
• Autonomy
  You operate without direction
  You design your week, work your pipeline, and surface decisions when they need to be made. You do not need a manager checking in — you need a founder who will get out of your way once trust is built.
• Nice to Have
  SaaS, HR tech, or recruitment
  Experience selling SaaS, HR tech, or recruitment-related products. Familiarity with ATS platforms, video interviewing tools, or hiring workflows. Existing network into HR, talent, or hiring decision-makers. None required, all valuable.

What you'll earn.

Leadership-tier compensation paid in USD. The engagement starts fractional at 15–20 hours per week and scales to full time as pipeline and revenue compound. Every engagement includes a $125 monthly add-on covering Leadership-tier incentive and standing transfer-fee adjustment — applied on top of base. Month-to-month. A performance bonus structure is on the table to be discussed as the engagement matures.