About this role.
Mattermost is hiring a senior enterprise Account Executive to win new logos and expand strategic accounts across the Americas, with a focus on defense-aligned and Fortune 500 buyers. The role owns the full enterprise sales cycle, including territory planning, outbound prospecting, discovery, demonstrations, executive engagement, negotiations, and closing. Success depends on building complex multi-stakeholder relationships across IT, security, procurement, and executive leadership while maintaining strong pipeline discipline in Salesforce. This U.S. East Coast-based, remote-first role requires consultative SaaS selling expertise and comfort with technical, security-focused buying environments.
Role DNA
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Job Complexity
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5/5Autonomy Level
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Core skills
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Sample interview questions
I begin by segmenting target accounts by strategic fit, potential value, technical environment, and buying triggers. I map key stakeholders, identify whitespace and likely use cases, define account-specific outreach sequences, and establish measurable pipeline-generation goals. I review results regularly and adjust prioritization based on engagement, opportunity quality, and conversion data.
I build a stakeholder map early and identify each group's priorities, risks, decision criteria, and influence on the buying process. I use a mutual action plan to align milestones, technical validation, commercial steps, and executive checkpoints. Throughout the cycle, I confirm compelling business outcomes and maintain multiple relationships so the opportunity does not depend on a single champion.
I would first understand the customer's operational workflows, security requirements, data-control needs, and integration landscape. I would connect the platform's deployment flexibility, private-cloud or on-premises capabilities, interoperability, and secure collaboration features to measurable risk reduction and operational outcomes. I would then involve technical partners to validate the architecture and create confidence in implementation.
I use MEDDPICC to validate measurable outcomes, identify the economic buyer, understand decision criteria and process, document procurement steps, assess pain, strengthen the champion, and evaluate the competitive landscape. If critical elements are missing, I create an action plan to close those gaps before forecasting the deal with high confidence. This keeps forecasts realistic and ensures the sales team is working on qualified opportunities.
I protect dedicated weekly blocks for prospecting and account research while using clear next steps and mutual action plans to keep active opportunities moving. I prioritize based on opportunity stage, strategic value, and likelihood of progress, but I do not allow late-stage work to eliminate pipeline generation. Consistent prospecting is essential to maintaining future coverage and reducing reliance on a small number of deals.
Mattermost is the leading collaborative workflow platform for defense, intelligence, security, and critical infrastructure. Trusted by the U.S. Department of War and Fortune 500s, our platform runs on-premises and in private clouds, delivering secure messaging, file sharing, workflow automation, audio/screenshare, and project management—all with full data and operational control. Mattermost powers high-stakes workflows across mission planning, real-time, real-world operations, DevSecOps, incident response, and cyber defense—enabling secure collaboration from tactical edge and DDIL environments to enterprise HQ. Teams operate across web, desktop, and mobile, with embedded interoperability for Microsoft Teams, Outlook, and Microsoft 365.
To learn more, visit www.mattermost.com
Mattermost is seeking a Senior Account Executive, Enterprise to own and grow a portfolio of strategic enterprise accounts across the Americas — with a sharp focus on net-new pipeline generation, executive-level engagement, and complex deal execution. This is a hunter-first role. You will be responsible for identifying and closing new enterprise logos, expanding Mattermost’s footprint within high-value accounts, and navigating multi-stakeholder buying processes across IT, security, procurement, and executive leadership. You’ll work closely with defense-aligned prospects and Fortune 500 customers who rely on Mattermost for mission-critical collaboration.
If you thrive in high-stakes enterprise sales environments, are energized by complex deals with real-world impact, and want to sell software that genuinely matters to the organizations that depend on it — this is your opportunity.
What You’ll Do
- Own a portfolio of enterprise accounts across the Americas, driving net-new revenue and strategic expansion within existing customers.
- Build and execute territory plans including target account mapping, whitespace analysis, and outbound prospecting strategies.
- Lead the full sales cycle from outbound prospecting and discovery through demo, negotiation, and close for enterprise deals.
- Engage confidently with VP- and C-level stakeholders across IT, security, procurement, and business units to position Mattermost as a strategic platform.
- Deliver compelling product demonstrations and value-based presentations tailored to technical, business, and executive audiences.
- Partner cross-functionally with Sales Engineering, Customer Success, Product, and Marketing to drive deal velocity and ensure successful customer outcomes.
- Lead contract negotiations, ensuring alignment between customer outcomes and Mattermost’s commercial objectives.
- Maintain rigorous pipeline hygiene, accurate forecasting, and account documentation in Salesforce.
- Represent Mattermost at industry events, conferences, and customer engagements relevant to defense, security, and critical infrastructure.
What We’re Looking For
- Proven enterprise sales experience in SaaS or enterprise software, with a demonstrated track record of closing complex, multi-stakeholder deals at the senior level.
- Based on the U.S. East Coast (required)
- Demonstrated ability to run a full sales cycle from cold outbound to close within large enterprise accounts ($100K+ ACV).
- Strong consultative selling skills — you ask great questions, listen deeply, and map solutions to business outcomes.
- Confidence and credibility engaging VP- and C-level stakeholders across technical and business functions.
- Experience delivering effective product demonstrations and articulating technical value to non-technical buyers.
- Proficiency with Salesforce; fluency in MEDDPICC or a comparable enterprise sales qualification methodology.
- Excellent written, verbal, and presentation skills; comfortable working asynchronously in a remote-first environment.
Nice to Have
- Experience selling into enterprise SaaS, cloud, or platform environments with complex technical buying cycles.
- Familiarity with cybersecurity, compliance, DevOps, or secure collaboration platforms — comfort navigating security and IT conversations with enterprise buyers.
- Experience working alongside technical teams such as Sales Engineers or Solution Architects to advance and close deals.
- Existing relationships or network within Fortune 500 IT, security, or engineering leadership.
- Background selling into highly regulated industries such as financial services, healthcare, or critical infrastructure.
- Prior experience at a high-growth, remote-first, or open-source software company.
How Success Is Measured
- Quota attainment: consistent achievement of enterprise ACV and ARR targets.
- Pipeline generation: self-sourced pipeline as a percentage of total pipeline created.
- Deal quality: average deal size, sales cycle length, and win rate across enterprise accounts.
- Executive engagement: multi-threaded relationships and documented executive alignment in target accounts.
- Cross-functional feedback: positive collaboration scores from Sales Engineering, Customer Success, and Product partners.
Why Mattermost
- Mission-driven work: Your deals directly support the organizations and missions that depend on secure, reliable collaboration — from the tactical edge to the enterprise.
- Remote-first culture: Work from anywhere in the U.S. with a globally distributed, high-trust team built for autonomy and ownership.
- AI-forward environment: We actively adopt and build AI-enabled workflows — you’ll have access to cutting-edge tooling to accelerate your productivity.
- Open source at the core: Be part of a vibrant community shaping the future of secure collaboration.
- High-growth opportunity: Strong momentum in the defense and enterprise markets, with meaningful equity upside as we scale toward our revenue goals.
Compensation
Mattermost takes a market-based approach to pay. Actual compensation may vary based on location, skills, experience, qualifications, and market conditions. This role requires the candidate to be based on the U.S. East Coast (Eastern Time Zone).
Target Salary Range: $105,000 to $145,000 USD, plus commission
#LI-KR1
Mattermost is an EEO Employer, we are a remote-first, open-source company.
We are continually working to expand our hiring in more countries and regions, ensuring compliance with local laws and regulations, which takes time.
Mattermost values your unique perspective—we welcome all applicants. We encourage individuals from all backgrounds to apply and are committed to assessing candidates based on their skills and qualifications. We do not tolerate discrimination against staff or applicants based on race, religion, national origin, age, disability, pregnancy status, veteran status, or other personal characteristics.
If you require accommodations during the interview process, please let us know—we’re happy to assist.
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