Director of Sales

The Opportunity

Brightflag is seeking a dynamic and results-driven sales leader to take our high-performing sales team to the next level. As Director of Sales, you will be both a strategic driver and a hands-on contributor with an ability to roll up your sleeves to support deals, coach Account Executives to consistently raise the bar, and shape the way we win in the market. You will collaborate closely with internal stakeholders to ensure seamless client experiences and shared wins. This is an exciting opportunity to make a meaningful impact in a fast-paced, high-growth environment, with the chance to influence both our revenue trajectory and the evolution of our sales culture.

What You Will Be Doing

• Leading, coaching, and inspiring a team of Account Executives across the US and EMEA to consistently exceed revenue targets.
• Own top-line new ARR targets for the team and drive execution against quarterly goals.
• Actively managing and advancing deals, stepping in when needed to accelerate closes.
• Balancing strategic planning with hands-on execution, switching seamlessly between the two as needed.
• Leveraging tools like Gong and sales data to monitor performance, identify bottlenecks, and drive continuous improvements in win rates and sales velocity.
• Partnering cross-functionally with Sales Consulting, Implementation, and Customer Success to deliver client success and retention.
• Implement best practices around qualification, objection handling, and closing strategies.
• Provide Voice of Customer insights to Product and Engineering.
• Partner with RevOps and Enablement to streamline tech stack, compensation plans, and onboarding.

Skills & Experience

To be successful in the role, you need:

• 5+ years of management experience leading high-performing SaaS sales teams in a fast-paced environment.
• Experience closing deals of varying sizes (Mid Market to Enterprise) while managing multiple opportunities simultaneously.
• Strong coaching skills with demonstrated success developing sales reps through call reviews, actionable feedback, and strategic guidance.
• Excellent relationship-building abilities, both internally and externally.
• Comfortable moving between big-picture strategy and direct deal execution.
• Experience managing distributed teams and understanding international sales dynamics.
• Proficiency in sales tools (e.g., Gong, Salesforce) and expertise in pipeline/forecast management.

Life @ Brightflag

We’re growing fast and so is the experience we can offer you:

• A huge opportunity to make a real impact, to shape what we do and where we are going.
• The exposure and challenge you need to learn, grow and progress your career in a rapidly growing environment.
• Complex technical and business problems to solve and the trust and autonomy you need to go and solve them.
• A sound, helpful team, in a friendly, values-driven and inclusive environment.
• Compensation range of $300k - $350k OTE.
• 401k plan with a company match.
• Comprehensive health insurance, life insurance and long term illness/income protection.

We are a diverse and inclusive bunch of people. We welcome diverse perspectives and people who make every day count and strive for constant improvement. We do not discriminate based on gender, ethnicity, sexual orientation, religion, civil or family status, age, disability, or race. 

Location & Eligibility

We are looking for a candidate who is happy to work a hybrid schedule with 2 to 3 days in the New York office.  

Your time is valuable. To help with your application, we advise that regrettably we cannot offer work permit sponsorship/ self sponsorship for this role. 

About Brightflag

Hi, we’re Brightflag, the AI-powered, enterprise legal management platform that helps corporate legal departments operate with greater clarity, efficiency, and control.

Powered by our patented AI, which was developed with over 100,000 hours of legal and engineering expertise, and supported by our best-in-class Customer Success teams, Brightflag enables in-house legal teams to streamline operations, manage matters and spend, and collaborate more effectively with outside counsel.

Today, Brightflag is trusted by leading global organizations and forms part of the Legal & Regulatory division of Wolters Kluwer, a global provider of professional information, software solutions, and services. You can learn more about Brightflag here.