Director of Sales Excellence

Smartsheet

For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. ABOUT SMARTSHEET Smartsheet is a leading enterprise platform for dynamic work, empowering organizations to plan, execute, and report on work at scale. Backed by multiple private equity firms, Smartsheet operates with the rigor, discipline, and growth orientation of a world-class PE-backed SaaS company. We are at a pivotal moment — accelerating our AI capabilities, evolving our operating model, and building the organizational infrastructure to scale intelligently. THE OPPORTUNITY Smartsheet is in the midst of a significant transformation. The company’s AI roadmap is fundamentally changing what our platform can do — and the pace of that innovation is accelerating. The opportunity in front of us is clear. The challenge is execution: how do we ensure that our revenue organization can lead the transition? As Sr. Director, Revenue Enablement, you will own that answer. This role is built around the need to deliver learning and enablement that keeps pace with our roadmap, and aligns every member of the GTM to key principles in value selling, customer value and AI solutions expertise. You will design and operate the systems, programs, and tools that make that happen. This role reports directly to the CMO and sits at the intersection of sales productivity, AI adoption, and commercial execution. It requires someone who combines the rigor of a data-driven operator with the creativity of a learning designer and the credibility to influence senior GTM leaders. The right candidate thrives in a high-velocity, PE-backed environment where speed, measurability, and ROI are non-negotiable. You are here to build an enablement machine. WHAT YOU WILL OWN Enablement Velocity & AI-Driven Sales Motion  * Design and operate a modern, AI-augmented enablement system that dramatically compresses time-to-productivity for new hires and time-to-adoption for new product capabilities. *  Build scalable, role-based learning programs that leverage AI tools — including adaptive learning platforms, AI-assisted coaching, and automated content delivery — to increase throughput without proportional headcount growth. *  Establish a repeatable motion for enabling the field on AI product releases: from launch readiness to certified competency, with measurable adoption milestones. Revenue Impact, Metrics & Strategy  * Define and own the success metrics that connect enablement activity to revenue outcomes — ramp time, win rates, pipeline conversion, expansion rates, and forecast accuracy.  * Build dashboards and reporting frameworks that make the ROI of enablement visible to the CMO and CRO, and that inform program decisions.  * Translate Smartsheet’s broader GTM strategy into quarterly enablement priorities with clear owners, milestones, and accountability. Field Readiness & Product Marketing Partnership  * Partner closely with Product Marketing to ensure that AI feature messaging is translated into crisp, field-ready narratives, objection handling frameworks, and competitive positioning.  * Own the motion that takes a product release from “launched” to “seller-certified” — designing the programs, content, and inspection cadences that make readiness a standard, not an exception. Coaching, Methodology & Execution Discipline  * Operationalize Strategic Value Selling methodology, supported by structured playbooks, AI-assisted call review tools, and inspection cadences. * Define and continuously evolve the enterprise B2B selling competencies required to win in Smartsheet’s market — including AI fluency as a core selling skill. *  Drive consistent execution of sales methodology, deal rigor, and pipeline hygiene through both programming and data-driven inspection. Content, Tools & Technology * Own the enablement content ecosystem: messaging frameworks, playbooks, competitive battlecards, training assets, and partner materials.  * Lead the evaluation, adoption, and optimization of AI-powered enablement tools — from conversational intelligence platforms to AI content generation and readiness scoring.  * Partner with Revenue Operations to ensure the enablement and sales technology stack is integrated, instrumented, and driving measurable seller productivity. Team Leadership * Build, inspire, and scale a high-performing Enablement organization, fostering a culture of accountability, continuous growth, and measurable impact. * Own and steward the Enablement budget, making strategic investment decisions that directly accelerate revenue growth and sales productivity. * Shape company-wide strategic direction as a senior leadership stakeholder, driving program decisions with a focus on operational excellence and measurable business outcomes. * Define and champion the policies, processes, and best practices that elevate Smartsheet's sales and marketing organization, influencing how the business operates at scale. * Other duties as assigned.  How You Will Drive Business Value The Sr. Director, Revenue Enablement is accountable for delivering measurable impact on commercial performance — not just managing programs. The expectation is that this role produces outcomes that are visible to the CMO, CRO, and the board: * Faster time-to-productivity: Reduce ramp time for new AEs and CSMs through structured onboarding and role-based learning programs that are AI-assisted and continuously optimized * Accelerated AI feature adoption: Shrink the lag between AI product releases and field readiness — ensuring sellers can demo, position, and sell new capabilities within weeks of launch, not quarters * Higher win rates and deal quality: Drive consistent application of sales methodology and competitive positioning, translating enablement investment into measurable improvement in conversion and deal size * Enablement ROI visibility: Build the reporting infrastructure that connects program activity to commercial outcomes, providing the CMO and CRO with clear, data-driven insight into what is working and what to invest in next What You Will Bring Required * 12+ years of progressive experience in sales enablement, sales productivity, or GTM strategy within enterprise B2B SaaS * Demonstrated track record of building scalable enablement programs that measurably improved ramp time, win rates, or pipeline conversion * Deep fluency with AI-powered enablement tools and genuine conviction that AI fundamentally changes how sales organizations learn and execute * Highly analytical: comfortable defining metrics, building dashboards, and using data to diagnose performance gaps and measure program impact * Strong cross-functional credibility — able to partner with and influence senior leaders across Sales, Marketing, Product, and Customer Success * Execution-oriented: equally comfortable setting strategy and rolling up sleeves to get programs built and running * Outstanding communication and executive presence — able to translate complex GTM challenges into clear, compelling recommendations for senior audiences * Bachelor’s degree required; MBA or advanced degree preferred Preferred * Experience in a PE-backed or sponsor-backed environment, with familiarity operating at the pace, rigor, and accountability PE ownership demands * Background in AI enablement or future-of-work strategy, particularly in organizations actively deploying AI/ML into core products or go-to-market motions * Prior experience at SaaS or enterprise software companies that have undergone significant product or GTM transitions * Familiarity with enterprise sales methodologies (Value Selling, Challenger, or equivalent) and how to operationalize them at scale Current US Perks & Benefits: * Employer subsidized medical/vision and dental coverage for full-time employees * 401k Match to help you save for your future (50% of your contribution up to the first 6% of your eligible pay) * Monthly stipend to support your work and productivity * Flexible Time Away Program, plus Sick Time Off * US employees are automatically covered under Smartsheet-sponsored life insurance, short-term, and long-term disability plans * US employees receive 12 paid holidays per year * Up to 24 weeks of Parental Leave * Personal paid Volunteer Day to support our community * Opportunities for professional growth and development including access to Udemy online courses * Company Funded Perks, including a counseling membership, local retail discounts, and your own personal Smartsheet account * Teleworking options from any registered location in the U.S. (role specific) Smartsheet provides a competitive base salary range for roles that may be hired in different geographic areas we are licensed to operate our business from. Actual compensation is determined by several factors including, but not limited to, level of professional, educational experience, skills, and specific candidate location. In addition, this role will be eligible for a market competitive incentive opportunity. US Base Salary Pay Range $187,500—$247,500 USD   Get to Know Us: At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together. Equal Opportunity Employer: Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, India, and Singapore. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.  If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.   #LI-Remote

Datadog

Datadog is looking for a visionary Senior Leader of Sales Engineering (SE) to lead and scale a high-performing team of SE Directors in North America across Enterprise, Majors, and Public Sector accounts. This is a strategic leadership role with regional and global impact. You will define the Sales Engineering strategy for North America and act as a regional voice in global discussions with Product Management, Engineering, and Go-To-Market teams—ensuring that customer needs in North America influence Datadog’s global direction.  At Datadog, we place value in our office culture - the relationships and collaboration it builds, and the creativity it brings to the table. We operate as a hybrid workplace to ensure our Datadogs can create a work-life harmony that best fits them. What You Will Do Executive Leadership & Organizational Growth * Recruit, develop, and lead a team 3rd line SE Directors, fostering a culture of technical excellence, customer-centricity, and continuous growth. * Define and drive the technical sales strategy across North America, and globally. * Set the vision, priorities, and operating model for Sales Engineering, ensuring alignment with Datadog’s business objectives and local market dynamics. * Partner with Sales Leadership to align on revenue targets, go-to-market initiatives, and strategic customer engagement across the region. * Represent North America Sales Engineering globally, ensuring regional perspectives and requirements are reflected in Datadog’s product roadmap and GTM planning. Customer Partnership & Advocacy * Act as a trusted advisor to C-level and senior technical executives, demonstrating how Datadog solves critical observability, performance, and security challenges, especially given the rapid business adoption of AI. * Provide executive support for high-stakes opportunities, offering guidance throughout complex sales cycles. * Serve as an executive sponsor for strategic customers across North America. * Promote value-based technical selling, empowering teams to deliver impactful business outcomes. Cross-functional Collaboration & Global Influence * Collaborate closely with Sales, Marketing, Product, Engineering, and Customer Success to align field execution and messaging. * Use customer and field insights to advocate for innovation and regional needs within Product and Engineering. * Influence Datadog’s product roadmap and go-to-market strategies through close collaboration with global stakeholders. Operational Excellence * Implement and scale pre-sales methodologies, tools, and KPIs to drive consistency and customer impact across North America. * Analyze team performance and regional trends to drive data-driven improvements. * Stay current on market trends, competitive landscape, customer pain points, and evolving partner ecosystems. Who You Are * 10+ years of experience in Sales Engineering, Solutions Architecture, or similar pre-sales leadership roles, with multiple years of SE leadership experience or second line leadership. * Proven expertise in enterprise SaaS, cloud, observability, AI, and security solutions, with a track record of driving technical sales success at scale. * Strong executive presence and ability to engage and influence C-level stakeholders in large, complex organizations. * Exceptional leadership, coaching, and team-building capabilities, with experience scaling high-impact teams. * Proven track record in building customer relationships and willing to get in the field and help with top down sale * Deep understanding of sales methodologies such as MEDDICC, Command of Message (CoM), or similar frameworks. * The general travel expectation is 25%, though during peak periods it may increase to 50% Datadog values people from all walks of life. We understand not everyone will meet all the above qualifications on day one. That's okay. If you’re passionate about technology and want to grow your skills, we encourage you to apply. Benefits and Growth :  * Best-in-breed onboarding * Generous global benefits * Intra-departmental mentor and buddy program for in-house networking * New hire stock equity (RSUs) and employee stock purchase plan (ESPP) * Continuous professional development, product training, and career pathing * An inclusive company culture, able to join our Community Guilds and Inclusion Talks Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. #LI-Hybrid Datadog offers a competitive salary and equity package, and may include variable compensation. Actual compensation is based on factors such as the candidate's skills, qualifications, and experience. In addition, Datadog offers a wide range of best in class, comprehensive and inclusive employee benefits for this role including healthcare, dental, parental planning, and mental health benefits, a 401(k) plan and match, paid time off, fitness reimbursements, and a discounted employee stock purchase plan. The reasonably estimated yearly salary for this role at Datadog is: $238,000—$349,000 USD ---------------------------------------------------------------------------------------------------------------------------------- About Datadog:  Datadog is the leading observability and security platform for the AI era, providing businesses with unified visibility across the technology stack to manage complexity at scale. It brings applications, infrastructure, data, models, and security into one place, using AI to detect and resolve issues before they impact customers. Trusted globally by Fortune 500 companies and high-growth AI leaders, Datadog enables businesses to move faster with clarity and confidence. Learn more about #DatadogLife on Instagram, LinkedIn, and Datadog Learning Center. ---------------------------------------------------------------------------------------------------------------------------------- Equal Opportunity at Datadog: Datadog is proud to offer equal employment opportunity to everyone regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, veteran status, and other characteristics protected by law. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. Here are our Candidate Legal Notices for your reference.  Datadog endeavors to make our Careers Page accessible to all users. If you would like to contact us regarding the accessibility of our website or need assistance completing the application process, please complete this form. This form is for accommodation requests only and cannot be used to inquire about the status of applications.  Privacy and AI Guidelines: Any information you submit to Datadog as part of your application will be processed in accordance with Datadog’s Applicant and Candidate Privacy Notice. For information on our AI policy, please visit Interviewing at Datadog AI Guidelines.

Cargurus

Who we are At CarGurus (NASDAQ: CARG), our mission is to give people the power to reach their destination. We started as a small team of developers determined to bring trust and transparency to car shopping. Since then, our history of innovation and go-to-market acceleration has driven industry-leading growth. In fact, we’re the largest and fastest-growing automotive marketplace, and we’ve been profitable for over 15 years. What we do The market is evolving, and we are too, moving the entire automotive journey online and guiding our customers through every step. That includes everything from the sale of an old car to the financing, purchase, and delivery of a new one. Today, tens of millions of consumers visit CarGurus.com each month, and ~30,000 dealerships use our products. But they're not the only ones who love CarGurus—our employees do, too. We have a people-first culture that fosters kindness, collaboration, and innovation, and empowers our Gurus with tools to fuel their career growth. Disrupting a trillion-dollar industry requires fresh and diverse perspectives. Come join us for the ride! Role overview We are seeking a Benefits Analyst to be based in our Boston, MA, global headquarters location, on a hybrid schedule. This role will be reporting to the Director of Benefits and will be responsible for the oversight and administration of several CarGurus’ North America Benefits programs and perks as well as heavy involvement in new initiatives. This role will collaborate closely with both internal and external stakeholders and partners to optimize benefits offerings and provide excellent service to employees. What you’ll do  * Participate in all areas of employee benefits in partnership with the rest of the team. Lead a few areas of benefits.  50% of the work to start will be managing leave and accommodation cases end-to-end, partnering with vendors to ensure timely and accurate execution, and clear collaboration and communication with HR Strategy Partners, claimant employee and their manager. * Provide guidance and education to employees and managers; act as a subject matter expert on benefits programs. * Monitor vendor performance, data, and reporting; identify issues and hold partners accountable to service levels. * Collaborate cross-functionally (People Operations, People Applications (HRIS), Payroll, Legal, vendors) to ensure smooth program delivery. * Maintain confidentiality while ensuring compliance with legal and company requirements. * Support audits, reporting, and analysis; identify trends and recommend improvements. * Contribute to projects and program enhancements, vendor RFPs, and key initiatives like Annual Open Enrollment. * Partner with the Benefits team to meet priorities and escalate when needed. * Create employee communications for assigned programs. * Maintain ~60% onsite presence, with flexibility during peak periods. What You’ll Bring * 3+ years of U.S. benefits experience, preferably in fast paced, growing tech environments. * Experience in some  functions of employee benefits administration, including health and welfare, well-being, life and disability, leaves, 401(k), and voluntary plans. Time off, leaves and accommodations administration experience, as well as a passion for well-being are a plus. * Proven examples of independently owning several areas of benefits responsibilities, including careful tracking, accountability and clear communication with all critical stakeholders a must. * Examples of working collaboratively in a team environment. * Affinity for educating and communicating on employee benefits, including presenting to audiences. * Appreciation for compliance and risk reduction with comfort in and knowledge of local, state and federal employee benefits regulations, such as ERISA, IRS, DOL, ACA, HIPAA, and COBRA. * Examples of successfully completing special projects on top of normal day to day responsibilities. * High level of integrity and discretion when handling sensitive employee information. * Robust analytical skills, with the ability to interpret data and make data-driven recommendations. * Attention to detail and accuracy. * Comfort and proficiency with computer software and HRIS systems (Google products and Workday experience a plus). The displayed range represents the expected annual base salary / On-Target Earnings (OTE) for this position. On-Target Earnings (OTE) is inclusive of base salary and on-target commission earnings, which applies exclusively to sales roles. Individual pay within this range is determined by work location and other factors such as job-related skills, experience, and relevant education or training. This annual base salary forms part of a comprehensive Total Rewards Package. In addition to benefits, this role may qualify for discretionary bonuses/incentives and Restricted Stock Units (RSUs). Position Pay Range $72,000—$91,000 USD Working at CarGurus We reward our Gurus’ curiosity and passion with best-in-class benefits and compensation, including equity for all employees, both when they start and as they continue to grow with us. Our career development and corporate giving programs, as well as our employee resource groups (ERGs) and communities, help people build connections while making an impact in personally meaningful ways. A flexible hybrid model and robust time off policies encourage work-life balance and individual well-being. Thoughtful perks like daily free lunch, a new car discount, meditation and fitness apps, commuting cost coverage, and more help our people create space for what matters most in their personal and professional lives. CarGurus may require in-person interviews as part of our hiring process, particularly for positions based in our Boston and Dublin offices. Candidates selected for an in-person interview will be notified in advance. Please be aware that travel expenses are the responsibility of the candidate. We welcome all CarGurus strives to be a place to which people can bring the ultimate expression of themselves and their potential—starting with our hiring process. We do not discriminate based on race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, or sexual orientation. We foster an inclusive environment that values people for their skills, experiences, and unique perspectives. That’s why we hope you’ll apply even if you don’t check every box listed in the job description. We also encourage you to tell your recruiter if you require accommodations to participate in our hiring process due to a disability so we can provide the appropriate support. We want to know what only you can bring to CarGurus. #LI-Hybrid