How to sell to Heads of Sales at Fintech companies in Canada
Heads of Sales in fintech companies in Canada are primarily measured on quarterly revenue growth. They respond positively to outreach that demonstrates a clear understanding of their sales pipeline challenges, such as high churn rates or difficulties in closing deals. Addressing these specific pain points in your communication can significantly increase your chances of receiving a response.
Written and maintained by the SoloRiff team, who build outbound software and run outbound with it. The figures below are our own: we measured 570 fintech company domains over public DNS on 2026-09-03. Last updated 2026-09-03.
What actually hurts
- high churn rates
- slow sales cycles
- inefficient lead conversion
- team turnover
The playbook
- 01
Identify churn rate spikes
Research your target companies for recent churn rate announcements or customer complaints. Use tools like G2 or Trustpilot to find reviews highlighting dissatisfaction. This helps you tailor your outreach to address their specific pain points directly.
- 02
Analyze recent funding rounds
Filter for fintech companies in Canada that have recently secured funding. Use Crunchbase or PitchBook to identify these firms. Targeting companies with fresh capital often indicates a willingness to invest in sales solutions to drive growth.
- 03
Connect via LinkedIn with insights
Send a connection request to the Heads of Sales, including a personalized note referencing a recent funding event or a churn spike. Mentioning their recent challenges shows you’ve done your homework and are genuinely interested in their success.
- 04
Follow up on engagement
If they accept your connection request, follow up with a message that references a specific challenge they face, such as closing deals faster. Ask for a brief chat to discuss solutions tailored to their situation, emphasizing your understanding of their needs.
- 05
Schedule a call after a relevant event
If they engage with your content or respond positively, propose a call within a week of their response. Timing your outreach around their recent challenges or successes can increase your chances of booking a meeting.
Can fintech companies even receive your mail?
We measured the DNS of 570 fintech companies, sampled evenly across company sizes, to see how many authenticate their own email. It matters in both directions: a domain that does not authenticate is a domain whose team is used to mail going missing — and if your own domain is in the gap, yours is the mail going missing.
Publishes a DMARC policy of quarantine or reject — the domain actually asks receivers to act on failures.
The gap is the finding: 34.3% of 1–10-person companies against 92.2% of the largest — 58 points apart. Small companies are where the unauthenticated domains are, and small companies are who most cold outreach is aimed at.
Where does your domain sit?
Same three lookups, run live against your domain. Nothing is stored and nothing is emailed to you.
How this was measured
Company domains were sampled within employee-count bands, then queried over public DNS for SPF (TXT at the apex), DMARC (TXT at _dmarc.) and MX. One domain per company, deduplicated. Anyone can reproduce any single row of this with dig.
DKIM is deliberately absent. A DKIM key lives under a selector that cannot be enumerated from outside the domain, so a company with flawless DKIM under a name we did not guess would be counted as having none. That would measure our guess list, not the industry.
Domains with no MX record are excluded rather than counted as failures — parked and redirect-only domains would otherwise drag every figure down and make the result an artefact of the sample.
Sampled within bands, so this describes the population of companies, not of employees: a 10-person company counts once, as does a 10,000-person one. Each band is at least 60 domains; bands below that are not published. Figures are percentages of the sample, not of the whole industry, and we publish no company names — only counts.
Measured 2026-09-03. Re-measured monthly.
The full census across every industry — sortable, with sample sizes, free to reuse under CC BY 4.0.
Subject lines that fit
- Addressing your churn challenges
- Insights on improving sales cycles
- Strategies for lead conversion
Questions
- Why do Heads of Sales in fintech ignore outreach about generic sales tools?
- Heads of Sales in fintech often receive numerous generic pitches. They prioritize solutions that directly address their unique challenges, such as high churn rates or slow sales cycles. Without specific relevance to their situation, outreach is likely to be overlooked.
- What factors influence a Head of Sales' decision to respond?
- A Head of Sales is more likely to respond if the outreach highlights a clear understanding of their current challenges, such as inefficiencies in their sales process or recent churn spikes. Tailoring your message to these specific pain points is crucial.
- How can I build trust with a Head of Sales in fintech?
- Building trust involves demonstrating industry knowledge and understanding their specific pain points. Sharing relevant insights or case studies that resonate with their experiences can position you as a valuable resource rather than just another vendor.
- What communication style do Heads of Sales prefer?
- Heads of Sales typically prefer concise and direct communication that respects their time. They appreciate straightforward messaging that quickly gets to the point, especially when discussing potential solutions to their pressing sales challenges.
Or have it run itself
SoloRiff does every step above on its own — finds the companies, finds the people, writes each of them individually, and handles the replies. Drop your URL and watch it work before you sign up for anything.
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