Enterprise Account Executive - Americas (East)

Ashby; Southwestern Ontario; On-site; CAD 368,350 - 429,741; Full time

Benefits offered by this job

Unlimited PTO

Generous equipment budget

Education budget

Job summary

Ashby is looking for a Sales Executive to manage enterprise accounts in Ontario, focusing on new customer acquisition and upselling existing clients. You need a proven track record of exceeding sales quotas of over $1M and closing substantial deals. Strong communication and the ability to navigate complex sales processes are essential. The position offers a competitive salary range of $270K - $315K, unlimited PTO, and an encouraging environment for personal growth.

Qualifications

• Multi-year track record of exceeding sales quotas in SaaS.
• Demonstrated ability to engage executives.
• Strong communication and problem-solving skills.

Responsibilities

• Manage the full sales cycle from pipeline generation to win.
• Focus on new logo acquisition through inbound and outbound efforts.
• Expand customer accounts for upselling.

Skills

Exceeding $1M+ quotas

Closing $100K+ ARR sales

Consensus building

Self-sourcing pipeline

Detail oriented

Problem solving

Tools

CRM systems

Job description

About Ashby

We’re building the next generation of enterprise software and we’re starting with a suite of products that empower talent leaders, recruiters, and hiring managers to be a driving force for revenue & efficiency via a holistic, data‑centric talent strategy. We are well funded and backed by great investors, including Y Combinator, Elad Gil and Lachy Groom. We have thousands of amazing customers, including Snowflake, OpenAI, Shopify, Ramp, Notion, and Zapier, and many others who we cannot name. We have a clear buyer persona and large target market, we already have multiple products to sell, revenue and headcount are growing 100% Y/Y, and we’ve only taken the first steps toward a much larger opportunity. This is the perfect time to join!

About This Role

You will help us win Enterprise accounts in Eastern and Central time zones by managing the full sales cycle from pipeline generation through to win. You can expect to own a curated list of excellent fit, high propensity accounts as well as a geographic territory with significant market opportunity. In this role, you’ll primarily focus on new‑logo acquisition via a healthy mix of inbound and outbound, while also covering a small number of customer accounts for expansion and upsell. Our emphasis is on your ability to excel in the areas listed below and your appetite for continuous growth & improvement.

Role Requirements

• You have a multi‑year track record of exceeding $1M+ quotas, selling complex SaaS technologies to large organizations
• You have closed many $100K+ ARR sales which require consensus building and executive engagement
• You have a demonstrated ability to win highly competitive opportunities by identifying pain and business impacts and connecting those to strategic initiatives of the leadership team
• You are a hunter at heart and are comfortable self‑sourcing a majority of your own pipeline
• You have a growth mindset and are excited to tackle the challenges of a high growth startup

You Could Be a Great Fit If

• You demonstrate mastery of clear communication. You ask questions with precision and can explain complex concepts in simple terms. You eschew business jargon.
• You skillfully guide prospects through their entire buying process—engaging the right stakeholders at the right time to create consensus for a strategic technology decision.
• You become both a product and industry expert. You create “Ah ha!” moments in collaboration with your Solutions Engineer to build momentum & solve customer‑specific challenges.
• Your peers describe you as detail oriented. You send timely & crisp follow‑up emails. You take pride in internal operations, like real‑time CRM updates.
• You have strong business acumen. You help customers connect the dots between technical problems and their business impact. You craft compelling cases for change.
• You are excited to land the biggest deals we’ve ever done. You are diligent and gritty and have demonstrated perseverance to win long, competitive sales cycles.
• You’re a creative problem solver and comfortable with some healthy ambiguity. You’ll help us refine our Enterprise go‑to‑market motion to maximize the segment’s results over time.
• You’re willing to travel for company events, customer meet ups and on‑sites.

You May Not Be a Great Fit If

• You dislike prospecting. Enterprise reps at Ashby are responsible for sourcing half or more of their pipeline to complement our robust inbound lead flow.
• You prefer to leave demos to the experts. While you can expect Solutions Engineering support, our most successful AEs are those with strong curiosity and deep product acumen.
• You’re more of a relationship builder who focuses on selling into the install base. This is primarily a new business oriented role.
• You’re a lone wolf. You prefer to go it alone in your pursuit of new business. We believe in a team‑selling sales model.

Bonus

• Familiarity with Talent Acquisition and HR tools and workflows
• A network that includes Heads of Talent whom you can tap into

Our Philosophy

• We spend a lot of time building best‑in‑class products since we believe a highly differentiated product is easier to sell.
• We aim to provide both product & industry expertise whenever we interact with prospects and customers.
• We strongly believe that small teams with very talented people (and the right work environment) deliver much better performance than teams with large headcount. We hire and compensate accordingly.
• We value a strong sense of ownership, principled thinking over experience, and thoughtful communication.

Interview Process

• Intro Call (30 min) – You’ll meet with a Recruiter to discuss your fit for the role and address questions about our market and solution.
• Written Exercise – You’ll complete a short take‑home assignment to showcase your outbound muscle.
• Experience Deep Dive (60 min) – You’ll walk the Hiring Manager through your career journey in some detail to highlight your experience, achievements, and points of learning to understand how you’ve developed into the professional you are today.
• Challenge Interview (90 min) – This will be made up of two parts:
  • Discovery and Demo Role Play (60 min)
  • Deal Strategy Discussion (30 min)

Benefits

• Sell a product that our customers are truly excited about
• Fairly set, achievable quotas. Typically, greater than 65% of AEs are at or above quota.
• Unlimited PTO with four weeks recommended per year
• Generous equipment, software, and office furniture budget. Get what you need to be happy and productive!
• 10‑year exercise window for stock options. You shouldn’t feel pressure to purchase stock options if you leave Ashby —do it when you feel financially comfortable.
• $100/month education budget with more expensive items (like conferences) covered with manager approval.
• If you’re in the US, top‑notch health insurance for you and your dependents with 100% of all premiums covered by us, Flexible Spending Accounts and 401K match. We also offer up to 12 weeks of fully paid family/parental leave for all caregivers.

Compensation Range: $270K - $315K

We run the end‑to‑end hiring process through our own platform and ensure a level playing field for all candidates. Reaching out to hiring managers or recruiters directly won’t improve your odds of success. Please focus your energy on the quality of your application.

Ashby provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.