Senior Enteprise Account Executive, Italy

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.

About the role:

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.

What You'll do:

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

About you:

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

Why you should join Contentsquare

We invest in our people through career development, mentorship, social events, philanthropic activities, and competitive benefits. We are always assessing the perks we offer to ensure we’re aligned with the employees' needs.

Here are a few we want to highlight:

Virtual onboarding, Hackathon, and various opportunities to interact with your team and global colleagues both on and offsite each year

Work flexibility: hybrid and remote work policies

Generous paid time-off policy (every location is different)

Lifestyle allowance

A Culture Crew in every country we’re based in to coordinate regular activities for employees to get to know each other and bond outside of work

Every full-time employee receives stock options, allowing them to share in the company’s success

We have multiple Employee Resource Groups, that offer a safe space for individuals who share common identities, life experiences, or allyship to connect, support one another, and passionately advocate for the issues close to their hearts

And more benefits tailored to each country

Your personal data is used by Contentsquare for recruitment purposes only. Read our Job Candidate Privacy Notice to find out more about data protection at Contentsquare and your rights. You can exercise your rights by using our dedicated Data Subject Rights Portal here.

Your personal data will be securely stored in our hosting provider’s data center in Oregon (US west). We have implemented appropriate transfer mechanisms under applicable data protection laws.

Contentsquare may use AI-assisted tools to help review and screen applications. All decisions involving hiring are made by human reviewers, and your personal data will be processed in accordance with our Candidate Privacy Policy.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.