How to sell to Heads of Sales at Legal tech companies
Heads of Sales in legal tech are primarily measured on quarterly revenue growth. They respond to outreach that demonstrates a clear understanding of the unique challenges in selling complex legal solutions, such as lengthy sales cycles and the need for compliance with legal regulations. Tailoring your message to highlight how you can streamline their sales process will capture their attention.
Written and maintained by the SoloRiff team, who build outbound software and run outbound with it. The figures below are our own: we measured 569 legal tech company domains over public DNS on 2026-09-03. Last updated 2026-09-03.
What actually hurts
- lengthy sales cycles
- complex compliance requirements
- difficulty in demonstrating ROI
- high customer churn rates
The playbook
- 01
Identify recent funding rounds
Look for legal tech companies that have recently secured funding. Use sources like Crunchbase or PitchBook to filter for companies that raised capital in the last 6 months. These firms are likely looking to scale their sales efforts and may be more open to discussing solutions.
- 02
Research their product offerings
Dive into the specific legal tech solutions they offer, focusing on contract management or law firm software. Check their website and product reviews to understand their strengths and weaknesses. This knowledge will allow you to tailor your outreach to address their specific needs.
- 03
Highlight compliance challenges
In your outreach, directly reference the common compliance challenges faced by legal tech sales teams, such as data privacy regulations. Acknowledge these hurdles upfront to show that you understand their landscape and can offer solutions that help navigate these issues.
- 04
Connect through industry events
Identify upcoming legal tech conferences or webinars where these professionals will be present. Use LinkedIn to connect with them before the event and mention your interest in discussing industry trends. This establishes a rapport and increases the likelihood of a follow-up conversation.
- 05
Follow up after initial outreach
If you don't receive a response within a week, send a follow-up email referencing recent industry news or changes that might impact their sales strategy. This demonstrates your ongoing interest and keeps the conversation relevant, increasing your chances of booking a call.
Can legal tech companies even receive your mail?
We measured the DNS of 569 legal tech 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: 24.3% of 1–10-person companies against 82.6% 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
- Navigating compliance in sales
- Boosting revenue in legal tech
- Streamlining your sales process
Questions
- Why do Heads of Sales in legal tech ignore outreach about sales automation tools?
- Heads of Sales in legal tech may ignore such outreach if they perceive it as irrelevant to their specific challenges. If the messaging doesn't connect directly to their unique sales cycle or compliance needs, it risks being overlooked. Tailoring your approach to address their pain points is crucial.
- What common objections do Heads of Sales have regarding new sales tools?
- Common objections include concerns about implementation costs, the potential disruption to existing workflows, and doubts about the ROI of new tools. They may also worry about the learning curve for their team and how quickly they can see results from the new solution.
- How can I effectively engage Heads of Sales at legal tech firms?
- Effective engagement often involves demonstrating a deep understanding of their specific challenges, such as compliance and lengthy sales processes. Sharing insights or case studies relevant to the legal tech industry can also establish credibility and pique their interest.
- What timing is best for reaching out to Heads of Sales in legal tech?
- The best timing is often at the beginning of a quarter when sales teams are setting new goals and strategies. Additionally, reaching out after major industry events or legal tech conferences can increase your chances of a response, as they may be more open to discussing new ideas.
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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