GTM Strategy and Operations Analyst - Boston

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 CarGurus is hiring a Senior Sales Data Analyst to support our Inventory & Data pillar as we build, sell, and scale the next generation of dealer software. You'll serve as a core analytical partner for a high-growth pillar, translating disparate signals from Salesforce, Gong, and internal product telemetry into the data foundations our go-to-market organization needs to scale. Your work will bridge the gap between complex raw data and the repeatable, high-impact reporting that drives execution across the full dealer journey with our products. You'll partner closely with Sales, Product, Engineering, and Operations leaders to build the data foundations behind a new team-selling motion and a growing software portfolio. It's ideal for someone who enjoys building in ambiguity, shaping new processes, and helping a business scale with the right metrics from the start. The ideal candidate is an advanced SQL practitioner who is equally comfortable partnering with Engineering on CRM and reporting design as they are coaching stakeholders on how to interpret and act on data. They're energized by being early to a new business and building from the ground up. WHAT YOU'LL DO BUILD THE PILLAR'S GTM ANALYTICS FOUNDATION * Own pipeline, install base, and churn reporting for the pillar's products, turning early prototypes into scalable, repeatable views. * Build demo-to-close analytics: demo volume, no-shows, source attribution, and downstream MRR impact. Surface insights from Gong customer conversations. * Lead analytics for new product launches, tracking adoption, attach, and retention from beta through GA. * Partner with Product Analytics to define KPIs and integrate product telemetry into go-to-market analysis. CHALLENGE PROCESS AND CLOSE SYSTEM GAPS * Pinpoint where our processes and Salesforce design don't line up, the gaps that make the new team-selling motion hard to track, attribute, and measure. * Don't take existing processes at face value: question the status quo, design better approaches, and drive solutions that make the business measurable by default. * Partner with Operations, Engineering, and Sales to streamline workflows and evolve CRM design for better tracking of pipeline, team selling, and clean revenue attribution. * Define and enforce data governance for key workflows (demos, onboarding, no-shows, opportunity tagging, quoting) so downstream reporting is trusted. DRIVE PROSPECTING AND POST-SALE INSIGHT * Build prospecting signals that surface high-potential dealers for each product, and partner with sales tool owners to wire them into the platforms reps use every day. * Manage capacity and supply-demand reporting for products like Sell My Car so teams prioritize the right markets. * Partner with Customer Success on dealer-level engagement tracking, surfacing adoption-risk and churn signals so account and product teams can intervene early. SET THE TECHNICAL STANDARD * Write production-grade SQL on Snowflake and partner with Analytics Engineering to productionize durable data assets in dbt. * Build and maintain dashboards across our BI and CRM analytics tools (Looker, Omni, Salesforce CRM Analytics) so insights live where leaders and reps work. * Keep Inventory analytics aligned with broader Sales Analytics standards and definitions across CarGurus. WHAT YOU'LL BRING * 5+ years in analytics, sales analytics, business intelligence, or data strategy, ideally in SaaS, technology, or consulting. * Bachelor's degree in business, finance, computer science, or a related field, or equivalent practical experience. * Advanced SQL and hands-on experience with cloud data warehouses (Snowflake strongly preferred). * Strong working knowledge of Salesforce, including its core data structures and how they support or limit selling motions. Experience with Gong data is a plus. * Experience with modern analytics tooling such as dbt, Looker, Omni, and Salesforce CRM Analytics. * Solid grasp of SaaS and recurring-revenue metrics: pipeline, attach, conversion, churn, retention, and MRR. * A proven ability to turn ambiguous questions into clear analyses and durable reporting with the judgment to build structure where processes and metrics are still taking shape. * Excellent communication and storytelling skills, with a track record of influencing senior stakeholders. * Comfort in a cross-functional, matrixed, fast-moving environment. * Bonus: interest or experience in the automotive marketplace, dealer software, inventory management, pricing, or sourcing products. WHY THIS ROLE You'll help shape how CarGurus brings a growing portfolio of software and data products to market, building the measurement and reporting infrastructure a new business needs to scale. You'll partner closely with leaders across Sales, Product, Engineering, and Operations, influencing strategy while creating the systems, metrics, and insights that guide key business decisions. If you enjoy building in ambiguity, driving meaningful change, and helping a business scale from the ground up, you'll thrive in this role. 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 $87,000—$109,000 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

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

Shift Technology

Shift delivers AI agents that transform insurers' most critical work. By combining deep industry expertise and unmatched data resources, Shift provides proven results that have earned the trust of hundreds of the world's leading insurers. Our insurance-grade AI is accurate, explainable, and secure—empowering human experts to move with unmatched speed, total confidence, and a renewed focus on the people they serve.        Your browser does not support the video tag. Our culture is built on innovation, trust, and a drive to transform the insurance industry through our SaaS platform. We come from more than 50 different countries and cultures and together we are creating the future of insurance. Learn more at www.shift-technology.com   We are looking for a data-driven Marketing & Campaign Operations Specialist to sit at the intersection of campaign execution, data engineering, and marketing performance. This role is not about simply running email blasts, launching ad campaigns, or enriching contact data; it is about building the architectural pipes that power our outbound and inbound marketing engines, and fine-tuning as you go. The ideal candidate possesses the analytical mindset of a marketing operations lead, with the communications, strategy, and autonomy of a growth marketer. You will be responsible for orchestrating multi-source data workflows and campaigns on behalf of field marketing, owning marketing infrastructure and the tech stack (e.g. HubSpot/Salesforce), and managing marketing budget tracking and performance reporting to justify continued marketing investment. What Your Impact Looks Like At Shift, we value ownership from day one. In this role, you will: Marketing Campaign Optimizations (40%) * Be the go-to marketing expert on all things digital, support field marketing in strategizing, creating, and reporting on all types of digital campaigns (email, display, search, and organic channels).  * Work with brand and project management to templatize as much of the campaign planning process as possible * Regularly report on campaign performance, implement testing scenarios as needed, document winning strategies, suggest opportunities for improvement, and share results with broader GTM stakeholders * Build robust campaign workflows and automations that allow for best-in-class digital experiences, personalizations, and insights  Marketing Operations & Infrastructure (30%) * Audit tool utilization across our marketing stack (including Contrast, Asana, Canva, and more), handling user management, integration upkeep, and new tool recommendations * Manage the lifecycle of marketing data flowing between HubSpot and Salesforce, ensuring strict data hygiene, crisp lead-to-account mapping, and seamless handoff processes * Research, select, and implement a data orchestration tool of record; ensuring marketing & sales data (contacts, leads, and accounts) are enriched and automated wherever possible * Work closely with Sales Operations and Sales Enablement to ensure marketing processes are documented and trained, share tool changes, release notes, and digital best practices with field marketing Budgeting, Reporting, and Analytics (30%) * Build and own the dashboards that track core marketing metrics (Pipeline, influence, impact, and ROI)  * Act as the primary gatekeeper for the marketing budget. Track monthly media spend (e.g., LinkedIn, Google Ads) and software expenses against our * Manage the annual planning process * Translate raw marketing data into strategic insights for leadership, clearly demonstrating how our data orchestration efforts translate to pipeline impact.   WHAT YOU'LL NEED TO SUCCEED We are looking for a Shifter who is... * Ops Fluent: You bring 3–5+ years of experience in Marketing Operations, RevOps, or Growth Marketing at a B2B SaaS or technology company. * Tech Savvy: You possess deep administrator familiarity with HubSpot and Salesforce, specifically regarding custom object mapping, routing rules, and workflow builders. * Data Architect: You have proven expertise building automated data tables, managing API connections, enrichment waterfalls, and manipulating unstructured data using orchestration tools like Clay or Zapier. * Growth Minded: You thrive on testing new automated techniques, welcome a high appetite for change, and are excited about using emerging AI tools to scale marketing systems. You actively look for ways to continuously improve workflows and help your peers grow. * Communicator with Impact: You can tailor highly technical data insights into structured, clear, and relevant stories for non-technical stakeholders or executives. You listen carefully to ensure mutual understanding before executing next actions. * Collaborative: You naturally partner with cross-functional teams across different countries, seeking out global strengths to deliver unified outcomes. You build long-term alignment and trust through consistent, transparent updates.   Interview Process: * Recruiter Interview * Hiring Manager Interview * Interviews with Marketing and Sales Ops Teammates * Case Study (Presentation and Panel Discussion) To support our permanent, full time employees at every stage of their careers and lives, we provide a competitive total rewards and benefits package. Here are the global benefits we’d like to highlight: * Flexible remote and hybrid working options * Competitive Salary and a variable component tied to personal and company performance * Multiple Learning and Development opportunities, including Focus Fridays, a half-day each month to focus on learning and personal growth * Generous PTO and paid holidays * Mental health benefits  * 2 MAD Days per year (Make A Difference Days for paid volunteering) Additional benefits may be offered by country, based on your eligibility - ask your recruiter for more information. Intern and Apprentice positions may receive some of these benefits - ask your recruiter for more details. AI tools are used to help review applications for this role. Read our AI in Recruitment Notice for what the AI considers, how to request a human review, and our most recent bias audit. At Shift we strive to be a diverse and inclusive workforce. We welcome applications from and hire people who will contribute to the diversity of our company, without regard to race, color, religion, marital status, age, national or ethnic origin, physical or mental disability, medical condition, pregnancy, genetic information, gender identity or expression, sexual orientation, or other non-merit criteria. Shift Technology is committed to providing reasonable accommodations for qualified individuals with disabilities in our application and employment process. Should you require accommodation, please email accommodation@shift-technology.com and we will work with you to meet your accessibility needs. Please be aware of scammers and only trust correspondence that comes from emails ending in "shift-technology.com". We will never do initial outreach to you via Whatsapp/Text/SMS, never ask for banking information or personal identification numbers (ex. Social Security Number) as part of our recruitment process. Shift Technology does not accept unsolicited CVs from recruiters or employment agencies in response to the Shift Technology Careers page or a Shift Technology social media post. Any unsolicited CVs, including those submitted directly to hiring managers, are deemed to be the property of Shift Technology.