
Contentsquare · Rome
Contentsquare is the all-in-one experience intelligence platform designed to be easily used by anyone who cares about digital journeys. With our flexible and sc...
Contentsquare is the all-in-one experience intelligence platform designed to be easily used by anyone who cares about digital journeys. With our flexible and scalable platform, organizations quickly get a deep understanding of their customers’ whole online journey.
We are a global leader in the experience analytics space, with a growing presence across 15 offices worldwide. We’re here to stay—and we’re looking for team members who are excited to drive impact and help us scale even further.
Our aim is to create an inclusive workplace where everyone learns and succeeds. Contentsquare has built a community of individuals who are daring, understanding, and deliberate. We invite you to join us in making the complex simpler—for our customers, their customers, and each other.
Important note: Be careful of scammers pretending to be from Contentsquare. We will never ask for money or contact you through random texts. Any communication from our in house Talent Acquisition team will only ever come from our contentsquare.com or @contentsquare-ext.com domain. For more information, visit our careers blog.
Contentsquare is building its footprint in Italy, and we're looking for a Senior Account Executive to own the Government and Enterprise segment. This means navigating the full complexity of public procurement (CONSIP, MEPA, framework agreements) while also running strategic enterprise cycles in the private sector.
Own the full sales cycle for Government (Central and Local PA) and Enterprise accounts in Italy, from prospecting through close
Self-source pipeline through your network, industry events, referrals, and targeted outreach — and coordinate with Marketing on ABM campaigns for strategic accounts
Maintain rigorous pipeline hygiene in Salesforce and deliver accurate revenue forecasts
Monitor and qualify public tenders across CONSIP, MEPA, and regional platforms
Coordinate internally with Sales Engineering, Legal, and Tender Management to produce competitive technical-economic proposals
Structure and manage RTI (Raggruppamenti Temporanei di Imprese) arrangements with System Integrators and technology partners where needed
Stay current on the Codice dei Contratti Pubblici and identify opportunities tied to PNRR funding
Build lasting relationships with decision-makers across the PA: Direttori Generali, Responsabili Transizione Digitale (RTD), and C-Level executives
Map Contentsquare's capabilities to real business problems — digital experience improvement, conversion, accessibility, performance — and connect those to measurable ROI
Lead internal deal teams (SE, Customer Success, Product, Legal) and keep everyone aligned on strategy and messaging
Act as a credible voice for Contentsquare in the Italian market, representing the product at industry events and in senior client conversations
10+ years in B2B or B2G sales, with meaningful time in enterprise or Government accounts managing complex, multi-stakeholder cycles
Fluent in Italian and English, written and spoken
Track record of hitting or exceeding quota
Comfortable navigating both procurement processes and executive relationships
Familiar with structured sales methodologies (MEDDIC, Challenger, SPIN, or similar)
Experience in SaaS, digital analytics, MarTech, or enterprise tech is a strong plus; curiosity about the space is a baseline requirement
As a Senior Enterprise Sales Engineer, you’ll serve as a trusted technical advisor and strategic partner to both customers and Sales. You’ll lead complex technical evaluations, align solutions to business outcomes, and help shape deal strategy in high-impact opportunities. This role goes beyond delivering demos - you’ll own the evaluation experience end-to-end, influence key stakeholders, and help drive successful outcomes across enterprise accounts. What You’ll Do: * Own the sales process in partnership with Account Executives by leading and shaping the technical strategy across opportunities from PG to Closed Won * Lead customer discovery to uncover technical challenges, business goals, and success criteria, then translate those needs into tailored Datadog solutions and measurable business outcomes * Deliver engaging product demos, technical presentations, and solution workshops that connect platform capabilities to customer outcomes for diverse stakeholder audiences including executives * Full ownership of the technical evaluations (POVs) end-to-end: scoping use cases and requirements, defining competitive success criteria, building a project plan with clear timelines, and holding all participants accountable to the process * Identify, develop, and leverage technical champions across multi-stakeholder environments, building a structured plan for champion cultivation and influence throughout the deal cycle * Contribute to product direction through active participation in structured product and engineering field feedback sessions, bringing field insights and customer patterns to PM and engineering teams * Drive operational excellence by ensuring activity, deal progress, and customer interactions are accurately documented and up to date in related systems * Identify and proactively resolve technical and organizational blockers by collaborating across Product, Support, and GTM teams before customers are impacted * Contribute to team enablement by mentoring peers, sharing best practices, and creating reusable assets that scale knowledge across the region Who You Are: * 7+ years of experience in Sales Engineering, Solutions Engineering, or a technical customer-facing role within an enterprise environment * Skilled at influencing and adapting communication across technical, business, and executive audiences * Advanced background in public cloud (AWS, Azure, GCP), Kubernetes, APM/tracing, security, developer experience, observability * Strong communication skills, with the ability to explain technical concepts to a range of audiences * A consultative, outcome - oriented approach to problem-solving and customer engagement * Demonstrated ability to manage multiple opportunities and priorities in a fast-paced environment * Experience mentoring peers or contributing to team enablement initiatives * Demonstrated capability of utilizing AI tooling and scaling it * Growth mindset of embracing change and being curious * Willingness to travel as needed to support customer engagements 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. ---------------------------------------------------------------------------------------------------------------------------------- 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.
Our Strategic Account Executives target and close new business with Datadog’s largest, most strategic customers and prospects. In this role you’ll be focused on uncovering the pain points organizations face as they operate in or migrate to a cloud environment at scale as well as delivering the appropriate Datadog solution. 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’ll Do: * Prospect into large Fortune 1000 companies while running an efficient sales process * Maintain, build and own specific relationship maps for your territory including existing relationships and aspirational contacts * Develop a deep comprehension of customer's business * Negotiate favorable pricing and business terms with large commercial enterprises by selling value and ROI * Handle existing customer expectations while expanding reach and depth into assigned territory * Demonstrate resourcefulness when faced with challenges that defy easy solution * Have intuitive sense of necessary steps to close business and gain customer validation * Identify robust set of business drivers behind all opportunities * Ensure high forecasting accuracy and consistency Who You Are: * Someone with 5+ years closing experience (mix of field selling within mid-market and enterprise) * Driven and have met/exceeded direct sales goals of 1M+ and operated with an average deal size of $100k+ * Able to demonstrate methodology to prospect and build pipeline on your own * Experienced in working for an innovative tech company (SaaS, IT infrastructure or similar preferred) * Experienced in selling into large Fortune 1000 companies with the ability to win new logos * Role requires regular travel to client sites, within your area and other regions, using various modes of transportation (car, train, air), depending on business needs. 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: * High income earning opportunities based on self performance * New hire stock equity (RSU) and employee stock purchase plan (ESPP) * Continuous professional development, product training, and career pathing * Sales training in MEDDIC and Command of the Message * Intra-departmental mentor and buddy program for in-house networking * An inclusive company culture, opportunity to join our Community Guilds * Generous and competitive medical benefits package * Retirement savings match * Pet adoption and insurance program Benefits and Growth listed above may vary based on the country of your employment and the nature of your employment with Datadog. #LI-SN3 #LI-Remote This is a remote position #LI-Remote ---------------------------------------------------------------------------------------------------------------------------------- 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.
About Us Sophos is a cybersecurity leader defending 600,000 organizations globally with an AI-driven platform and expert-led services. Sophos meets organizations wherever they are in their security maturity and grows with them to defeat cyberattacks. Its solutions combine machine learning, automation, and real-time threat intelligence with frontline human expertise from Sophos X-Ops to deliver advanced, 24/7 threat monitoring, detection, and response. Sophos offers industry-leading managed detection and response (MDR) alongside a comprehensive portfolio of cybersecurity technologies — including endpoint, network, email, and cloud security, extended detection and response (XDR), identity threat detection and response (ITDR), and next-gen SIEM. Together with expert advisory services, these capabilities help organizations proactively reduce risk and respond faster, with the visibility and scalability needed to stay ahead of evolving threats. Sophos goes to market with a global partner ecosystem, including Managed Service Providers (MSPs), Managed Security Service Providers (MSSPs), resellers and distributors, marketplace integrations, and cyber risk partners, giving organizations the flexibility to choose trusted relationships when securing their business. Sophos is headquartered in Oxford, U.K. More information is available at www.sophos.com. Role Summary As a Senior Enterprise Account Executive will sell to and manage relationships with named end user accounts within the UK Public Sector of 1001+ users, fulfilling through the channel. You will actively generate and pursue opportunities to achieve sales quotas. With customers you will create and implement strategic account plans focused on attaining enterprise-wide deployments of Sophos products and services.This role will focus on UK Public Sector customers principally around the London and South of England but potentially across the UK