Who you are

- 6+ years of SaaS sales experience, including selling hosting-related solutions; managed hosting or WordPress hosting experience strongly preferred

- Demonstrated success selling sophisticated, high-value solutions with longer or more consultative deal cycles

- Experience selling to agencies, mid-market customers, or technical buyers

- Strong discovery, consultative selling, and negotiation skills

- Strong business acumen with the ability to connect customer needs to commercial outcomes

- Excellent communication skills across both technical and non-technical audiences

- Strong technical fluency, comfort, and credibility discussing WordPress, hosting, infrastructure, and platform-related concepts

- Proven ability to negotiate creatively, manage complexity, and solve problems in a way that creates value for both the customer and the business

- Strategic mindset with the ability to shape deal strategy, prioritize effectively, and operate with a high level of autonomy

- Collaborative working style and a track record of partnering well across sales, marketing, product, support, and technical teams

- Adaptability, sound judgment, and a proactive, results-oriented approach

- Ability to manage multi-stakeholder conversations and non-linear deal processes

- Comfort translating technical platform capabilities into clear business value

- Strong judgment and prioritization skills in a fast-paced, evolving workplace

- Proficiency with CRM systems (e.g., HubSpot) and disciplined pipeline management

- Comfort using AI-assisted sales tools to support research, preparation, follow-up, and deal analysis

- Experience selling hosting-related solutions; managed hosting or WordPress hosting strongly preferred

- Experience selling to agencies, developers, or infrastructure-aware customers

- Experience working in sales environments that leverage AI for efficiency and insight

What the job involves

- Pressable is seeking an experienced, strategic, and consultative Sales Account Executive (SAE) to help drive growth across larger agency and mid-market customers

- You’ll own complex sales opportunities end-to-end, from deep discovery through negotiation and close, and serve as a trusted advisor to customers with sophisticated performance, scale, and workflow requirements

- This is a senior individual contributor role designed for someone who thrives in longer sales cycles, multi-stakeholder environments, and consultative selling motions. The SAE role is intentionally structured to leverage AI as a force multiplier for research, preparation, and insight, while keeping human judgment, relationship-building, and decision-making at the center of the sales process

- You will report to the Head of Sales & Enablement and work closely with Solutions, Support,



and Product partners to ensure high-quality execution across strategic opportunities

- Own and manage larger, more complex agency and mid-market opportunities from discovery through close

- Build and manage relationships with both technical contacts and executive or business decision-makers

- Position Pressable’s platform as a long-term strategic partner for agencies and mid-market customers

- Lead deep technical and business discovery to understand customer goals, constraints, and success criteria

- Lead sophisticated opportunities involving multiple stakeholders, technical requirements, custom commercial structures, and non-standard deal terms

- Act as the quarterback across the deal cycle, coordinating technical experts and internal partners to move opportunities forward efficiently

- Deliver compelling presentations, solution walkthroughs, and business conversations tailored to the customer’s needs

- Develop proposals, pricing recommendations, and commercial packages that align customer requirements with company goals

- Lead contract and negotiation strategy in partnership with leadership, balancing creativity, customer value, and sound business judgment

- Maintain comprehensive market awareness, including customer needs, competitive dynamics, and industry trends, and use those insights to strengthen deal strategy

- Lead competitive positioning against alternative hosting platforms and infrastructure solutions, clearly articulating Pressable’s differentiation in performance, support, and partnership

- Support successful onboarding and identify expansion opportunities by maintaining strong post-sale relationships with customers

- Contribute to new business development through a mix of pipeline conversion, relationship-building, and proactive opportunity creation

- Proactively build and execute strategic outbound plans into high-value target accounts, including named account mapping and executive-level outreach

- Own an individual revenue quota across new logo acquisition and strategic expansion within larger agency and mid-market segments

- Maintain disciplined pipeline management, forecasting, and deal documentation in HubSpot

- Ensure opportunities are properly qualified, structured, and progressed with clear next steps

- Identify expansion and long-term growth opportunities within high-value accounts

- Use AI tools to support account research, discovery preparation, deal analysis, and follow-up drafting





- Leverage call transcripts and AI-generated insights to identify objections, patterns, and next steps

- Apply judgment to AI outputs, knowing when to rely on automation and when human decision-making is required

- Collaborate with Solutions, Support, and Product teams to improve playbooks, pricing guidance, and feedback loops for strategic deals

- Contribute structured product and market feedback based on real customer conversations

- As a part of our fully distributed team, you can live in a wide range of locations around the world. Effectiveness in this role will mean occasionally shifting hours across weekends and odd hours to best coordinate with our global team

Benefits

- Professional Development · “I will never stop learning” is part of our company creed. From leadership development to improving your writing skills, we have a comprehensive list of programs and resources available to everyone, and we’re also happy to pay for any hardware, software, books, or conferences that promote continued learning.

- Career Coaching · Coaching sessions to help you set and achieve qualified goals are available for all Automatticians – team members and team leads. This benefit resets each calendar year.

- Time off · Our open vacation policy (no set number of days per year) is designed to help you to be at your best! There is no minimum or maximum, but we encourage you to take at least 25 days of time off per year.

- Home Office · We offer home office setup and coworking allowances. Working from a coffee shop? You can use your coworking allowance for the requisite latte!

- Wellness · We offer mental wellness benefits including an Employee Assistance Program, a monthly subscription to a mindfulness app (including Calm, Headspace, Ten Percent Happier, Waking up, and Insight timer), and virtual ergonomic consultations and access to a wealth of virtual ergonomic tips, stretch videos and yoga exercises.

- Parental leave · Open parental leave (including maternity, paternity, LGBTQ+, and adoption for all parents). If you’ve been with Automattic for 12 months, your leave up to 6 months is fully paid.

- Anniversary Awards · Paid three-month sabbatical encouraged every five years and other cool anniversary surprises.

- Automattic Stock · Check out Buying and selling Automattic Stock!

- Life Insurance · Company-sponsored life insurance.

- Compensation · We attract talent around the world and pay global salary ranges. We prioritize internal equity and review your pay every 12-18 months.

- Sabbatical · Working at Automattic provides numerous opportunities to learn new skills, grow in your career, and have a significant and positive impact on the lives of millions. It also offers the rare (and juicy!) benefit of a paid, three-month sabbatical every five years.

📌 Senior Sales Account Executive (Canada)
🏢 Automattic
📍 Canada