[All remote jobs](https://jobicy.com/jobs.md)[![Ashby logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/08/63864ee6-221.png)](https://jobicy.com/company/ashby.md)[Ashby](https://jobicy.com/company/ashby.md) # Head of Mid Market Sales, Americas AI Summary Ashby is seeking a second-line sales leader to lead its Mid-Market sales organization across the Americas. The role manages three sales managers initially, expanding to four, and is accountable for regional revenue performance, talent development, and execution of the sales plan. This leader will partner with Revenue Operations and Marketing to open new verticals, improve pipeline generation, and support expansion toward a multi-product SaaS platform. The position requires substantial experience leading managers in a high-growth B2B SaaS environment and shaping data-driven go-to-market strategy.[Apply for this job](#job-application)[View company](https://jobicy.com/company/ashby.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 340k–407,500 / yrDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceSeniorPublished11 Nov 2026Apply before11 Dec 2026Listing views20Application actions0Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### About [Ashby](https://jobicy.com/company/ashby.md) Sales at Ashby is a unique opportunity to sell a [product customers genuinely love](https://www.ashbyhq.com/customers) during an AI-fueled market expansion. Over 5,000 companies rely on Ashby including Shopify, Snowflake, OpenAI, Bolt, and Notion, and our business is durably growing faster than 100% year-over-year. [We’re well funded](https://www.ashbyhq.com/blog/culture/series-d), and on a path to profitability. That’s exceptionally rare for a company at our scale, and puts us in the top 10% of benchmarks. We have, in just a few years, replaced incumbents Greenhouse and Lever more than 500 times each, clear evidence of strong product-market fit and a meaningful opportunity to help modern teams move beyond legacy recruiting software. Ashby replaces 3-5 tools in a consolidation & efficiency play that’s equally loved by recruiters and CFOs. We’re known as a [clear AI-leader](https://www.ashbyhq.com/ai) in the recruiting space. And the market opportunity is growing. We are rapidly extending from a best-in-class recruiting product toward a multi-product platform, expanding upmarket, into new industries, and internationally. For sales reps, that means a large market full of legacy tools, and a product portfolio that creates room for both new business and expansion. This is a chance to participate in how a category-defining company wins in its next phase of growth. We are equally intentional about how we build the business. We have established a remote-first, high-performing sales organization that rewards learning and accountability. We [use data to set achievable quotas](https://www.ashbyhq.com/blog/culture/how-we-think-about-sales-quotas-and-incentives-at-ashby), and reward sustained impact with competitive compensation and meaningful upside. We prioritize coaching and career development, with AEs advancing to Enterprise & Leadership roles in just a few years — 38% of the team who have been here more than a year have been promoted or taken on a new role! You will work with people who care about craft, customer outcomes, and winning together—without sacrificing the trust, autonomy, and balance required to do your best work over the long term. Don’t just take my word for it, [see what the team has to say](https://www.repvue.com/companies/Ashby) about working here. About this Role To scale Ashby into the hundreds of millions of ARR, we are seeking a senior B2B SaaS sales leader to lead our high performing Mid-Market sales team in AMER. The start date of this role will be Q1. This is currently a second-line leadership role, initially overseeing a team of three managers growing to four in Q2. This strategic leadership role reports directly to our Head of AMER Sales ([Leigh Brown](https://www.linkedin.com/in/leighfitzgerald/)). There are three primary responsibilities that this senior sales leader will take on: * Build an Amazing Team. Hire, lead, coach, and develop the North American sales team including Managers and Account Executives. * Execute on the Sales Plan. Be accountable for the region’s revenue and results. Foster programs that ensure high-caliber execution across all segments. * Unlock new Opportunities. Partner with peers in Revenue Operations and Marketing, to expand Ashby’s Serviceable Addressable Market to clear a path to $200M+ in ARR in 2027 through a focus on new verticals and products. You will have a significant impact in defining our go-to-market strategies to help us achieve our ambitious growth plans. You can read more about our[Sales Team here](https://docs.google.com/presentation/d/1vLg_KNx1AT5IndMtn6uehdzUxp3Z1CKlRhY6TVDQ_rM/edit#slide=id.g32cab2b3b62_0_470). If we are even moderately successful, we’ll have an incredible growth story to tell in just a few years! ### You could be a great fit if: * 💼 You’ve been a second line sales leader at a $100M+ high growth SaaS company * 🥇 You have a proven track record of hiring high performing Managers and AEs who quickly move the needle. You’re also comfortable making timely performance management decisions. * 📊 You have managed a Mid-Market sales-led go-to-market motion (100-1000 FTE). * 📈You are well versed in modern pipeline generation practices and programs that ensure sustainable pipeline coverage for substantial YoY growth. * 🤝 You’re an expert collaborator who builds relationships internally and can drive change initiatives forward to improve overall operations. * 🤓 You connect the dots quickly. You can evaluate the health of the business, and hone in on the most impactful areas to drive performance and bend the growth curve. Your team trusts you to provide practical advice and consultation to navigate challenging or complex issues * ⚙️ You are adept at developing sales strategies for multi-product platforms and competitive rip-and-replace deals ### You shouldn’t apply if: * You haven’t managed managers at a high growth SaaS business * Your primary focus is the forecast and extracting information from your direct reports. At Ashby, your job is to bend the curve, not just report the numbers. ### Our Philosophy Here are a few key points that should give you an idea of what it is like to be a Sales Leader at Ashby: * We’re highly collaborative and we believe in a team-based sales motion to maximize our win rates on high impact deals * We believe in developing subject matter expertise (not just on our product but also the talent acquisition space broadly) which allows us to provide a differentiated buyer experience * We continue to make material investments in engineering and product because we know at the end of the day, having the best products makes winning new customers easier We value a strong sense of ownership, principled thinking over decades of experience, and thoughtful & clear communication both internally and with customers. [Please read more about our operating principles here](https://www.ashbyhq.com/blog/culture/ashbys-operating-principles). ### Interview Process Our interview process is designed so you can showcase your achievements and points of learning and apply those to a practical exercise. We’ll provide you with sample customer calls and pipeline data so you can develop a well informed perspective on our product and the Mid Market segment. You’ll have opportunities to ask questions of our team throughout. The interview process for this role is four rounds in the following order: * Intro Call (30 min) – You’ll meet with Steph Fish, our TA Manager for Sales, to discuss your fit for the role and address questions about our market and solution * Experience Deep Dive (1 hr) – You’ll walk Leigh through your leadership experience in some detail to highlight your achievements, and points of learning. * Panel Presentation (1 hr) – We’ll provide you with Ashby data and seek your perspective on the business and focus areas. You’ll discuss your approach to leadership, hiring and developing managers and sales execution. * Final Round (2.5 hrs) – You’ll have a set of four interviews with a range of cross-functional leaders ### Benefits * You’ll get the time to do things the right way; we put a lot of emphasis on high quality work and avoid quick hacks as much as possible. * You get to sell a product that our prospects & customers are truly excited about. * 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. * Unlimited PTO with four weeks recommended per year. Expect “Vacation?” in our one-on-one agenda until you start taking it 😅 * Twelve weeks of fully paid family leave in the US. We plan to expand this to employees in other countries as situations arise. * Generous equipment, software, and office furniture budget. Get what you need to be happy and productive! * $100/month education budget with more expensive items (like conferences) covered with manager approval 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. 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. Ashby is committed to a fair and transparent hiring process. We confirm that this advertisement is for an active, existing vacancy within our organization. Please be advised that we may use artificial intelligence-driven tools to assist our recruitment team in screening, assessing, and selecting candidates for this position. Show more [Apply now >](https://jobicy.com/jobs/161285-head-of-mid-market-sales-americas.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a senior, second-line leadership position with direct accountability for regional revenue, manager performance, and strategic market expansion. Success requires operating effectively across sales execution, hiring, coaching, pipeline strategy, and cross-functional change initiatives. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$373,750US market range (per year)$300k–$450k0$495.00k AI insightThe employer discloses an annual base salary range of USD 340,000 to USD 407,500, with a midpoint of USD 373,750. This range is plausible for a senior second-line Mid-Market SaaS sales leader in the US and Canada, although variable compensation may be additional and is not included in the stated base-pay figures. Estimated annual market base pay for comparable leadership roles is USD 300,000 to USD 450,000. ## Core skills Skills and capabilities most closely associated with this opportunity. [B2B SaaS Sales Leadership](https://jobicy.com/jobs?search_keywords=B2B%20SaaS%20Sales%20Leadership.md)[Mid-Market Sales](https://jobicy.com/jobs?search_keywords=Mid-Market%20Sales.md)[Second-Line Management](https://jobicy.com/jobs?search_keywords=Second-Line%20Management.md)[Revenue Strategy](https://jobicy.com/jobs?search_keywords=Revenue%20Strategy.md)[Sales Coaching](https://jobicy.com/jobs?search_keywords=Sales%20Coaching.md)[Manager Development](https://jobicy.com/jobs?search_keywords=Manager%20Development.md)[Account Executive Hiring](https://jobicy.com/jobs?search_keywords=Account%20Executive%20Hiring.md)[Pipeline Generation](https://jobicy.com/jobs?search_keywords=Pipeline%20Generation.md)[Go-to-Market Strategy](https://jobicy.com/jobs?search_keywords=Go-to-Market%20Strategy.md)[Sales Forecasting](https://jobicy.com/jobs?search_keywords=Sales%20Forecasting.md)[Revenue Operations Collaboration](https://jobicy.com/jobs?search_keywords=Revenue%20Operations%20Collaboration.md)[Cross-Functional Leadership](https://jobicy.com/jobs?search_keywords=Cross-Functional%20Leadership.md)[Performance Management](https://jobicy.com/jobs?search_keywords=Performance%20Management.md)[Strategic Account Selling](https://jobicy.com/jobs?search_keywords=Strategic%20Account%20Selling.md)[Market Expansion](https://jobicy.com/jobs?search_keywords=Market%20Expansion.md) Sample interview questionsHow have you improved the performance of a Mid-Market sales organization through frontline managers?I begin by aligning managers on a small set of measurable leading indicators, such as pipeline coverage, conversion rates, deal quality, and rep ramp progress. I then combine regular business reviews with coaching plans that address the root cause of performance gaps, while holding managers accountable for developing their teams rather than simply reporting forecasts. Describe how you would evaluate the health of Ashby's Mid-Market business during your first 90 days. I would assess attainment trends, pipeline creation, stage conversion, sales-cycle length, win-loss patterns, segmentation, capacity, manager effectiveness, and customer feedback. I would use that analysis to identify the few highest-leverage constraints, validate them with frontline conversations, and establish a prioritized operating plan with clear owners and success measures. What is your approach to hiring and developing high-performing sales managers? I hire managers who can diagnose business problems, coach individual sellers, recruit strong talent, and create accountability without micromanaging. Development starts with clear role expectations, calibrated performance standards, observed coaching, peer learning, and regular feedback tied to both team results and leadership behaviors. How would you partner with Marketing and Revenue Operations to enter new verticals? I would align on the target customer profile, buyer pain points, competitive alternatives, and proof points needed for each vertical. Together, we would test focused messaging, build account lists and pipeline programs, measure early funnel performance, and rapidly refine the playbook before scaling investment. How do you balance aggressive growth targets with sustainable sales execution? I use ambitious goals alongside transparent capacity planning, realistic pipeline assumptions, and disciplined inspection of leading indicators. Sustainable execution comes from investing in enablement, manager capability, customer value, and repeatable processes rather than relying on short-term pressure or one-off heroics. 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