Account Executive

• We're seeking our first Account Executive to join our founding team. This isn’t just a job- it’s a chance to help build and define how startups buy legal services in a completely new way.

• You’ll work directly with the founding team to own the full sales cycle — from first conversation to close — while helping shape our go-to-market strategy, messaging, and sales processes from the ground up. You’ll be on the front lines with founders, understanding their needs and translating Shepherd’s hybrid legal + software model into clear, compelling value.

• As an early member of the team, you’ll have meaningful ownership over revenue outcomes and play a critical role in building a repeatable, scalable sales engine.

• This is a rare opportunity to help define a new category: AI-native legal services for startups.

• Own the full sales cycle from inbound/outbound lead to close

• Run discovery calls with founders and operators to understand legal needs, risks, and priorities

• Clearly articulate Shepherd’s value proposition- combining legal services with software- in a way that resonates with startups

• Drive pipeline progression: qualification, demos, proposals, and closing

• Partner closely with the founding team to refine messaging, pricing, and positioning based on customer feedback

• Build and optimize sales processes, playbooks, and CRM workflows (HubSpot or similar)

• Collaborate with marketing and growth to improve lead quality and conversion

• Develop relationships with founders, operators, and startup ecosystem partners

• Track and report on pipeline, conversion metrics, and revenue performance

• Help define the foundation for a high-performing sales organization

• 4–8+ years of experience in B2B sales, preferably in SaaS, fintech, or services-based businesses

• Proven track record of closing deals and hitting/exceeding quota

• Experience owning the full sales cycle in a high-velocity environment

• Strong discovery and consultative selling skills

• Excellent communication and storytelling ability — especially with founders and executives

• Comfort operating in an early-stage, ambiguous environment

• Familiarity with CRM tools (e.g., HubSpot, Salesforce) and pipeline management

• Experience selling to startups (pre-seed through Series B)

• Background in legal tech, fintech, or selling complex / hybrid service + software offerings

• Experience helping build sales processes or being an early GTM hire

• Existing network within the startup or venture ecosystem

• Entrepreneurial mindset- You thrive in ambiguity and enjoy building from zero

• Ownership mentality- You take full responsibility for pipeline and revenue outcomes

• Customer-first- You focus on solving real problems, not just closing deals

• Operator mindset- You think in systems and help build repeatable processes

• High urgency- You move quickly and follow through relentlessly

• Adaptable- You’re comfortable iterating on messaging, product, and process in real time

• Competitive compensation: $90,000 – $120,000 base salary + commission (OTE $150,000 – $200,000+)

• Meaningful equity: Early-stage ownership with significant upside

• Direct impact: Shape Shepherd’s go-to-market strategy and revenue engine

• Category creation: Sell a differentiated product in a new and evolving market

• Professional growth: Opportunity to grow into sales leadership as the company scales

• Mission-driven work: Help democratize access to high-quality legal services for startups

We believe ambitious outcomes are possible. We explore unconventional ideas, test them rigorously, and act on the data- learning fast without distraction or comparison.

Mediocrity has consequences. We set the highest standard in our execution, judgement, and how we show up everyday- because excellence compounds.

Speed and urgency are habits that when modeled consistently and scaled through automation, become contagious across the team, the product, and our customers.

Legal work runs on trust, not features. We earn trust by being responsive, transparent, and accountable to our customers- particularly when it’s uncomfortable.

We pair high standards with empathy and ambition with humanity. Respect and integrity are NOT separate from winning- they are how we win.

We are an equal opportunity employer and are committed to building a diverse and inclusive workplace. We do not discriminate on the basis of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected characteristic.