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About the Role
Seeking the first Account Executive to join the founding team, with an opportunity to build and define how startups purchase legal services. This role involves owning the full sales cycle, shaping go-to-market strategy, and playing a critical role in building a scalable sales engine for AI-native legal services.
Responsibilities
- 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
Requirements
- 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
Skills
- B2B sales
- SaaS sales
- Fintech sales
- Services-based sales
- Closing deals
- Quota attainment
- Full sales cycle ownership
- High-velocity sales
- Discovery calls
- Consultative selling
- Communication
- Storytelling
- CRM tools (HubSpot, Salesforce)
- Pipeline management
- Sales process building
- Messaging refinement
- Pricing strategy
- Positioning
- Customer feedback analysis
- Sales playbook development
- CRM workflow optimization
- Lead quality improvement
- Conversion rate optimization
- Relationship building
- Performance tracking
- Revenue reporting
Location
- Remote
Work Type
- Full-time
Experience Level
- 4-8+ years
- Early-stage
- Founding team
Salary/Compensations
- $90,000 – $120,000 base salary + commission (OTE $150,000 – $200,000+)
Benefits
- Competitive compensation
- 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
About the Company
- 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.
Equal Opportunity
- 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.