Senior Enterprise Account Executive - East

Contentsquare · Remote · US

Open 2 days

New Business + Account Growth: you win new customers and grow existing ones.

Pay (base or OTE?): $300K–$340K
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: 3d ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon Contentsquare's careers page

Apply on Contentsquare →

The job

What you'd do

Sell Contentsquare's software to very big companies across North America, mostly winning new customers and also selling more to existing ones. You'll do much of your own prospecting.

What you'd sell

Shows companies where customers get stuck on their site

When a company runs a website or app, it needs to know where people get stuck while shopping or signing up. The problem is, people who hit a snag just leave, and the team running the site often can't see where or why. Contentsquare shows how customers move through a website or app and where they run into trouble, so the team can fix those spots and keep more people going.

In plain English, from their own job posts. Something wrong? Tell me · More Sales & marketing companies →

Who you'd sell to

Not stated in the posting.Ask: “Who's the economic buyer, and who else is in the deal?”

Where deals come from

Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Worth a look

Solid on the basics. Use the first call to fill in the gaps.

Pay: Base is listed but not OTE. Ask what the variable is and how many people hit it.
Transparency: Shares 1 of 5. Mentions territory. Ask about quota, attainment, deal size and sales cycle.
Time on market: Open 2 days.
Company hiring: 7 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Yellow lights

Base or OTE? Ask. They posted a number but didn't say if it's base salary or total pay with commission. It's high for a base, so ask which it is.

Green lights

None spotted.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
3.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
4.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
5.

Before You Apply

Find out where you fit, and where you don't, before you hit submit.

Why I built it this way ↓

Most résumé tools try to make you look like a match. I'd rather help you find out if you are one.

Nothing made up.
Nothing goes on your résumé that you didn't do. If a line would need a number you didn't give me, I ask. I don't guess. On Braun Board it's checked in code, not just promised.
Curiosity before conclusions.
If the job wants something your résumé doesn't show, I ask before I assume. Plenty of sellers have done the thing and just never wrote it down.
Sorting, not selling.
Some jobs won't line up with what you've done. Finding that out before you apply isn't a loss. It's an hour back, spent on a job that fits.
No score.
A match score tells you how well you copied their words. It doesn't tell you whether you'd be good at the job, or happy there.

It's the same way I teach selling. We don't control who says yes. We do control where we spend our time, and whether everything we say is true.

Josh

1 Is the job worth it?

Worth a look. Solid on the basics. Use the first call to fill in the gaps.

No red lights. 1 thing the posting doesn't say, worth asking on the first call.

See the full Braun Read

2 Where you fit

Upload once, see where you fit on any job.

What people say about working at Contentsquare ↓

Got an offer from Contentsquare? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Rather talk it through? Call or text me: 954-695-0844 (text)

Full posting

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 contentsquare.com 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-value opportunities through strategic prospecting, territory planning, account research, and effective engagement with key stakeholders. Navigate complex enterprise sales: Lead sophisticated, multi-stakeholder sales cycles, building business cases that connect Contentsquare’s solutions to customer priorities and measurable business outcomes. Engage executive stakeholders: Establish credibility and build lasting relationships with senior executives, decision-makers, and other key influencers across target accounts. Drive account growth: Identify opportunities to expand relationships with existing customers through cross-sell, upsell, and strategic account development. Communicate customer value: Articulate Contentsquare’s value proposition and differentiate our platform in a competitive market, connecting customer challenges to tangible business impact. Collaborate cross-functionally: Partner with Solutions Consulting, Customer Success, Finance, Legal, and other internal teams to deliver a cohesive customer experience and advance opportunities. Champion the customer: Bring customer insights and market feedback back to the business to inform product innovation, go-to-market strategy, and continuous improvement. Contribute to regional growth: Bring an entrepreneurial mindset, strong commercial judgment, and a results-driven approach to expanding Contentsquare’s presence across North America. What You’ll Bring 7+ years of successful B2B SaaS sales experience, with a strong track record of acquiring new enterprise customers and driving new revenue. Demonstrated success managing complex, consultative enterprise sales cycles, from initial prospecting through contract negotiation and close. Experience building and maintaining a healthy pipeline, prioritizing opportunities, and managing multiple deals across different stages of the sales process. Proven ability to build relationships with senior executives and C-suite stakeholders, influence buying decisions, and navigate complex organizational structures. Strong business acumen, with the ability to uncover customer challenges, develop compelling value propositions, and connect solutions to measurable business outcomes. Excellent communication, presentation, negotiation, and relationship-building skills. An entrepreneurial mindset and the ability to operate independently, take ownership, and adapt in a fast-paced, evolving environment. A customer-first approach, with a genuine interest in building long-term partnerships and driving customer success. Nice to Have Experience selling MarTech, digital experience, customer experience, analytics, or other technology solutions to enterprise organizations. Familiarity with the challenges enterprise businesses face when optimizing digital journeys and improving customer experiences. 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 Won BuiltIn Best Places To Work 2026! Contentsquare is an equal opportunity employer. Qualified applicants will receive consideration for employment without regard to sex, gender identity or expression, sexual orientation, race, color, religion, national origin, disability, protected veteran status, age, or any other characteristic protected by law. 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.

Apply →