Legalsense - Sr Director of Sales

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Legalsense is seeking a Senior Director of Sales to build and scale a repeatable revenue engine across the Benelux and Nordic markets, reporting to the CEO. This player coach role blends strategic leadership with hands on execution in a scaling SaaS environment, owning the sales playbook, forecasting discipline, and pipeline management while guiding a small Netherlands and Nordics sales team. You will stay active in deals, lead senior stakeholder conversations, and design outbound and partner led motions to diversify the pipeline while owning core metrics such as coverage, velocity, and forecast accuracy. To apply, demonstrate 3+ years leading B2B SaaS sales into professional services in European markets, with ACV €5K-€25K, a hunter mindset, early stage growth experience, and fluent English; NL based preferred, willingness to travel, onsite in the Netherlands.

COMPANY DESCRIPTION

Legalsense builds practice management software that helps law firms in the Netherlands run their practices more effectively - from client and matter management to time tracking, billing, and beyond. We're a small, close-knit team based in the Netherlands, and we care deeply about the experience of the legal professionals who rely on our software every day. Our work is guided by a genuine commitment to our customers and to building something they trust. If you like being close to the product, the customer, and the people you work with, you'll feel at home here.

JOB DESCRIPTION

Legalsense is seeking a Senior Director of Sales to build and scale a repeatable revenue engine across Benelux and Nordic markets. Reporting directly to the CEO, this player/coach leader will introduce forecasting rigor, pipeline discipline, outbound generation, and scalable sales processes while helping the company expand its international go-to-market capabilities.

Today, the business operates with a strong inbound motion and a growing commercial team, creating a significant opportunity for a hands-on sales leader to build operational structure, strengthen pipeline visibility, and establish repeatable outbound and partnership-driven growth motions.

This role is ideal for someone who enjoys balancing strategic leadership with day-to-day execution inside a scaling SaaS environment. The ideal candidate combines strong SaaS sales leadership experience with an analytical, process-oriented mindset and a willingness to operate directly inside deals, coach sellers, and improve sales execution across the organization.

You're Excited About This Opportunity Because You Will:

• Build and own the sales playbook — defining the processes, operating cadence, forecasting discipline, and pipeline management rigor the team needs to scale predictably
• Lead a small team of sellers across the Netherlands and Nordics, coaching on pipeline, deal progression, and consultative selling into law firms and professional services buyers
• Stay hands-on in deals - running senior stakeholder conversations, stepping in to advance or close opportunities, and modeling the sales rigor and customer engagement standards you expect from your team
• Build new pipeline channels — designing and launching outbound and partner-led motions that reduce reliance on inbound demand and create more predictable pipeline generation
• Own the commercial metrics — tracking pipeline coverage, conversion rates, deal velocity, forecast accuracy, and overall pipeline health to drive decisions in the absence of a dedicated RevOps function
• Partner with leadership to shape international go-to-market strategy, including expansion into new European markets, evaluation of new customer segments, and regional sales execution priorities
• Hire, coach, and develop sellers over time as the team grows — bringing structure, accountability, and operational discipline without losing the agility of a small, tight-knit environment

We're Excited About You Because:

• You have led a small sales team (3–8 people) in a B2B SaaS environment while staying actively involved in deals - you are comfortable as a player-coach and don't disappear into management
• You have 3+ years of experience selling software into professional services markets - legal, accounting, consulting, or adjacent - and understand the long buying cycles, senior stakeholder dynamics, and risk-averse buyer mindset that come with it
• You have sold B2B SaaS in European markets with ACV in the €5K–€25K range and understand the nuances of SMB and lower mid-market sales motions
• You are based in the Netherlands (Amsterdam or Randstad area strongly preferred) and are comfortable being present with the team and customers in the region
• You are a hunter at heart - energized by new logo acquisition and experienced building outbound and partner channels, not just managing inbound
• You are analytical and process-oriented - you know how to read a pipeline, diagnose velocity problems, and build accountability into a team without micromanaging
• You have joined a company early in its sales motion (pre-€20M ARR) and brought structure and repeatability without losing momentum
• Experience in Benelux or Nordic markets is a strong plus - familiarity with regional buyer behavior, sales culture, and market dynamics will help you hit the ground running
• Dutch fluency is not required; strong English communication skills are essential

Location: This role is based in the Netherlands. Amsterdam/Randstad area strongly preferred; open to candidates elsewhere in Benelux with willingness to travel frequently.

Secure Candidate Experience: All official emails and messages regarding your application will come from an @legalsense.nl or @alpinesg.com email address. We will never ask for sensitive personal information such as Social Security numbers, banking information, or payment details during the hiring process.