Hybrid
Remote
SaaS
himalayas
About this role
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.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 or @contentsquare-ext.com domain. For more information, visit our careers blog.
About the Role
As a Senior Enterprise Account Executive, you will play a key role in driving Contentsquare’s growth across North America by identifying, developing, and closing strategic enterprise opportunities. You’ll own the full sales cycle, from prospecting and pipeline development through negotiation and close, while building trusted relationships with senior decision-makers and C-suite executives.
This is an opportunity for a proven enterprise sales professional who thrives in a competitive, fast-paced environment, takes an entrepreneurial approach to building pipeline, and knows how to translate complex business challenges into compelling solutions.
Working cross-functionally with Solutions Consulting, Customer Success, Finance, Legal, and other teams, you’ll help customers realize the value of Contentsquare while contributing to our continued growth in the region.
What You’ll Do
Drive new business: Own the end-to-end sales cycle, from prospecting and qualification to negotiation and close, with a strong focus on acquiring new enterprise customers. Build and manage pipeline: Develop a robust pipeline of high-va
Commission Structure
Base Salary
Not disclosed — ask in interview
Commission
Structure not specified
OTE
$340k (range: $300k–$340k)
Ramp Period
Not mentioned — clarify timeline
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Prospecting
Outbound-Heavy
Self-sourced pipeline via cold outreach
Buyer Persona
C-Suite
Selling to executive decision-makers
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAccount Executives are the revenue engine of any sales organization — this role will require strong pipeline management and closing skills.
Top SaaS reps often earn significant upside through accelerators once quota is exceeded.
This remote-friendly role provides geographic flexibility while maintaining access to a SaaS market.
With OTE potential exceeding $340k, this role sits in the top tier of sales compensation. Expect rigorous performance expectations and a proven track record requirement.
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