About the Company – Pioneering the Future of Talent Management
At Ashby, we are building the next generation of enterprise software that empowers talent leaders, recruiters, and hiring managers to become powerful drivers of revenue and operational efficiency. Our data‑centric, holistic talent strategy platform is trusted by nearly 2,000 forward‑thinking organizations—including industry powerhouses such as Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier.
Backed by world‑class investors like Y Combinator, Elad Gil, and Lachy Groom, Ashby enjoys the financial stability and strategic support needed to innovate at speed. Our revenue and headcount are growing at an unprecedented 100% year‑over‑year, and we are just beginning to unlock the massive market opportunity that lies ahead. Joining us now means becoming part of a high‑impact, hyper‑growth journey where your contributions will be visible, valued, and rewarded.
Why This Role Matters – Enterprise Sales at Scale
The Enterprise Account Executive – AMER (East) is the engine that drives new‑logo acquisition across the Eastern and Central time zones of the United States. In this fully remote position, you will own a curated portfolio of high‑propensity accounts, lead the entire sales cycle from prospecting to close, and collaborate closely with our Solutions Engineering, Customer Success, and Product teams to deliver unparalleled value to our customers.
Our ideal candidate thrives on complex, multi‑stakeholder deals, enjoys the challenge of building consensus among C‑level executives, and possesses a relentless appetite for personal and professional growth. If you are motivated by the prospect of closing $100K+ ARR contracts, shaping an emerging go‑to‑market strategy, and becoming a key player in a fast‑scaling SaaS business, this is the role for you.
Key Responsibilities – Own the Full Enterprise Sales Journey
- Territory Management: Develop and execute a strategic plan for the Eastern and Central U.S. territory, targeting high‑value accounts that align with Ashby’s ideal customer profile.
- Pipeline Generation: Prospect, qualify, and nurture leads through a balanced mix of inbound engagement and outbound outreach, ensuring at least 50% of your pipeline is self‑sourced.
- Consultative Selling: Conduct deep discovery calls, articulate Ashby’s value proposition, and craft tailored business cases that link talent‑management challenges to measurable ROI.
- Stakeholder Alignment: Identify, engage, and influence senior decision‑makers—including CEOs, CHROs, and VP of Talent—through strategic conversations that drive consensus.
- Deal Structuring & Negotiation: Lead complex contract negotiations, navigate pricing models, and close multi‑year ARR deals exceeding $100K.
- Collaboration with Solutions Engineers: Partner with SEs to deliver compelling demos, proof‑of‑concepts, and “aha” moments that address specific customer pain points.
- Account Expansion: While primarily a new‑logo role, you will also manage a small portfolio of existing customers to uncover upsell and cross‑sell opportunities.
- CRM Excellence: Maintain real‑time updates in Salesforce (or equivalent) and ensure accurate forecasting, pipeline health, and activity reporting.
- Market Feedback Loop: Relay insights from prospects and customers back to product, marketing, and leadership to continuously refine positioning and feature priorities.
- Travel (up to 40%): Attend key industry events, customer on‑site meetings, and internal training sessions as needed.
Essential Qualifications – What We Need to See on Your Resume
- Proven Quota Attainment: Minimum three years of experience consistently exceeding $1M annual quota in a SaaS environment.
- Complex Deal Experience: Demonstrated success closing $100K+ ARR contracts that required multi‑level executive sponsorship and consensus building.
- Strategic Insight: Ability to translate technical challenges into strategic business outcomes and articulate a clear ROI narrative.
- Communication Mastery: Exceptional verbal and written communication skills, with a talent for simplifying complex concepts without resorting to jargon.
- Detail‑Oriented Execution: Track record of delivering timely, crisp follow‑up communications and meticulous internal documentation.
- Resilience & Grit: Proven perseverance in long, competitive sales cycles; comfortable navigating ambiguity and turning it into opportunity.
- Team‑Selling Mentality: Comfortable collaborating in a cross‑functional environment, leveraging internal experts to drive deals forward.
Preferred Qualifications – Nice‑to‑Have Extras
- Experience selling talent acquisition, HR tech, or workforce management solutions.
- Established network of senior talent acquisition leaders (Heads of Talent, CHROs, etc.) in the target geography.
- Familiarity with modern recruiting metrics, OKRs, and data‑driven talent strategies.
- Prior exposure to high‑growth startup environments, particularly those backed by venture capital.
Core Skills & Competencies – The DNA of Success at Ashby
- Consultative Sales Methodology: Mastery of MEDDPICC, Challenger, or similar frameworks.
- Executive Presence: Ability to hold credible, strategic conversations with C‑suite leaders.
- Analytical Acumen: Comfort with data analysis, forecasting, and building business cases using ROI calculators.
- Product Curiosity: Eagerness to become a subject‑matter expert on Ashby’s platform and the broader talent‑tech landscape.
- Collaboration: Strong partnership skills with SEs, Customer Success, Marketing, and Product teams.
- Adaptability: Thrive in a fast‑changing environment and pivot strategies based on market feedback.
- Time Management: Ability to juggle multiple opportunities, prioritize effectively, and meet aggressive activity targets.
Career Growth & Development – Your Path at Ashby
We invest heavily in the professional advancement of our people. As an Enterprise Account Executive, you will have access to:
- Structured Learning Program: $100/month education budget, plus manager‑approved sponsorship for conferences, certifications, and industry events.
- Mentorship & Coaching: Regular one‑on‑one sessions with senior sales leadership to refine techniques, troubleshoot challenges, and map out long‑term career trajectories.
- Leadership Opportunities: High performers are fast‑tracked into senior AE, team lead, or Sales Manager roles, with clear pathways to Director of Sales and beyond.
- Equity Participation: 10‑year stock option exercise window with no pressure to purchase immediately; you can exercise when financially comfortable.
- Cross‑Functional Exposure: Work closely with product, marketing, and customer success, giving you a holistic view of the business and positioning you for broader leadership roles.
Work Environment & Culture – What It’s Like to Be an Ashby Team Member
At Ashby, you will experience a culture built on four foundational pillars:
- Ownership & Impact: Small, high‑performing teams where every voice matters and each individual’s contributions directly influence company outcomes.
- Principled Thinking: Decisions are driven by data, logical reasoning, and customer empathy—not merely seniority.
- Thoughtful Communication: We prize clarity, transparency, and brevity. Internal communications are concise and action‑oriented.
- Continuous Innovation: Our product team spends the majority of its time building differentiated solutions, ensuring you have a compelling story to sell.
Our remote‑first policy means you can work from anywhere in the United States, with a flexible schedule that respects work‑life balance. We provide a generous equipment budget—laptops, monitors, chairs, and any software you need—to create a home office that feels like a professional hub.
Compensation, Perks & Benefits – Competitive, Transparent, and Generous
- Competitive Base Salary + Uncapped Commission: Aligned with industry benchmarks for enterprise SaaS roles, with clear attainment thresholds.
- Quota Attainment: Over 65% of AEs consistently meet or exceed quota, reflecting realistic targets and strong support.
- Unlimited PTO: We trust you to manage your time; a recommended minimum of four weeks per year is suggested for recharging.
- Health & Wellness: 100% premium coverage for you and your dependents—including medical, dental, and vision—plus Flexible Spending Accounts.
- Retirement Savings: 401(k) plan with company match to help you build long‑term financial security.
- Equipment & Home Office Stipend: Budget for high‑quality hardware, ergonomics, and software tools.
- Equity Options: Stock options with a long exercise window, aligning your financial upside with company growth.
- Learning & Development: $100 monthly education allowance, conference sponsorship, and internal training programs.
- Diversity & Inclusion: An EEO employer committed to fostering an inclusive environment where every background, perspective, and ability is celebrated.
Interview Process – Transparent, Fair, and Insightful
We believe a great hiring experience is a two‑way street. Our interview framework is designed to assess fit while giving you deep insight into Ashby’s mission, team dynamics, and growth trajectory.
- Recruiter Screen (30 min): Discuss your background, motivations, and answer any initial questions about the role.
- Sales Writing Exercise: Demonstrate your ability to craft compelling messaging and articulate value propositions.
- Hiring Manager Interview (60 min): Deep dive into your experience, approach to complex deals, and cultural alignment.
- Challenge Interview (75 min): Real‑world scenario that assesses your strategic thinking, objection handling, and collaborative problem solving.
- Final Round (45 min): Meet with senior leadership to discuss vision, long‑term growth, and answer any remaining questions.
All candidates receive detailed feedback at each step, ensuring a respectful and constructive experience.
Ready to Make an Impact? – How to Apply
If you are excited to champion a market‑leading talent platform, build relationships with Fortune‑500 leaders, and accelerate your career in a high‑growth SaaS environment, we want to hear from you. Apply today and take the first step toward joining a team that is redefining how organizations attract, retain, and develop top talent.
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