Senior Enterprise Account Executive

Cyara; Montreal (administrative region); On-site; CAD 150,000 - 250,000; Full time

Job summary

Cyara is seeking a Sr. Enterprise Account Executive to drive strategic deals with large enterprises from Montreal, Canada. You will own territory strategy, manage complex, consultative sales cycles, and act as a trusted advisor to buyers including C-level executives.

You will lead demand creation, develop territory and account plans, and collaborate with global teams to ensure success while meeting quota targets. Exceptional SaaS sales background required with strong negotiation and CRM skills.

Qualifications

• 8+ years of proven SaaS sales experience.
• Experience in UCaaS/CCaaS or related industries such as telecom or CX platforms.
• Professional demeanor with a problem-solving attitude.
• Demonstrated consultative, solution-based selling in complex cycles.
• Experience selling at the C-level.
• Collaboration with colleagues globally to drive success.
• Efficient time and calendar management.
• Solid technical acumen to translate product strengths into business value.
• Strategic thinker focused on outcomes and customer success.
• Self-motivated with urgency and excellence.
• Excellent communication, presentation, and negotiation skills.
• CRM proficiency (Hubspot, Salesforce or similar).

Responsibilities

• Hit quota and execute territory and close planning.
• Develop a plan for achieving quotas within a fiscal period.
• Sell into the region with ICP and buyer personas in mind.
• Act as trusted advisor, offering insights and solutions.
• Update planning tools for cross-functional deal reviews.
• Address obstacles and report progress to management.
• Demonstrate product alignment with prospect pain points.
• Forecast opportunities with a 10% margin by week 8.
• Counter competitors and leverage discounts strategically.
• Execute campaigns and generate high-quality leads.
• Articulate Cyara value and competitive advantages.
• Negotiate to secure contracts and POs.

Skills

SaaS sales

UCaaS/CCaaS experience

Consultative selling

C-level selling

CRM tools (Hubspot, Salesforce)

Global collaboration

Tools

Hubspot

Salesforce

Job description

As the global leader in AI-powered customer experience assurance, we help some of the world's most recognized brands deliver seamless, reliable, and engaging interactions across voice, digital, messaging, and AI-powered channels. Every year, our platform helps optimize hundreds of millions of customer journeys, ensuring businesses can confidently deliver exceptional experiences at scale.

As enterprises race to deploy agentic AI, the defining question is no longer whether AI can handle customer interactions, it’s whether those interactions can be trusted. Cyara is the confidence layer that answers that question, testing AI agents with AI agents to detect hallucinations, validate decisions, and ensure compliance before failures ever reach your customers.

Joining Cyara means helping shape the future of customer experience, partnering with some of the world’s biggest brands, and working alongside passionate, talented people who are committed to making every customer interaction better.

You're a fit for our Sr. Enterprise Account Executive role if you've blown away sales goals at a previous role, and are looking for an entrepreneurial sales environment. Ideally, you are a creative problem solver, looking to quickly digest Cyara’s product suite, and help build a world class organization. Experience in the B2C CCaaS space is a BIG bonus. You must be comfortable navigating complex and consultative sales processes (Fortune 500-1000 companies), handling deal sizes averaging $150K-$1M. This is an opportunity to have an immediate impact: Come build with us!

Let's talk about the role and responsibilities:

• Let’s get this one out the way immediately – hit your quota!
• Develop a comprehensive plan for achieving assigned quotas within a fiscal period, incorporating Territory Planning, Strategic Account Planning, and Close/Win Planning
• Possess experience selling into your applicable region having understanding of the ICP and buyer personas within that region.
• Act as a trusted advisor to clients, offering insights, recommendations, and solutions that address their specific business challenges and objectives. Create demand!
• Regularly update and maintain planning tools to facilitate cross-functional discussions, deal reviews, and engagement with Executives
• Recognize expectations and proactively address any obstacles that may hinder meeting those expectations, communicating with your manager as needed
• Quickly become knowledgeable on the Company’s product with an ability to demonstrate it in alignment with a prospect’s pain points
• Assess opportunities in the pipeline to derive accurate forecasts for a given time period, ensuring forecasts are within a 10% +/- margin at week 8 forecast
• Address competitor advantages raised by buyers and successfully sell against competitors
• Execute company campaigns, meet outbound call and email targets with high-quality leads that can be converted into opportunities
• Possess a deep understanding of the value provided by Cyara solutions and services, emphasizing its competitive advantages
• Recognize negotiation opportunities and effectively use trading and bargaining techniques with customers to achieve mutually beneficial outcomes
• Appropriately leverage discounts and promotions as economic levers during negotiations
• Demonstrate the ability to overcome obstacles and secure contract agreements and purchase orders

Let’s talk about your skills/expertise:

• 8+ years of proven SaaS sales experience.
• Strongly preferred: Candidates with experience in UCaaS, CCaaS, or adjacent industries such as telecommunications, customer experience platforms, or contact center technologies.
• Professional demeanor with a positive attitude, focusing on problem-solving and "How can I" rather than dwelling on challenges.
• Demonstrated experience in consultative selling, solution-based selling, and complex sales cycles.
• Experience selling at the "C" level.
• Collaboration with colleagues globally, proactively contributing to the success of both your immediate team and the larger organization.
• Efficiently manage your time and calendar to ensure the completion of essential tasks and responsibilities.
• Solid technical acumen in order to add value to customer discussions and translate product strengths into business benefits.
• Strategic thinker with a results-oriented mindset and a passion for driving customer success and satisfaction.
• Self-motivated and proactive with a sense of urgency and a commitment to excellence.
• Excellent communication, presentation, and negotiation skills, with the ability to influence and persuade at all levels of an organization.
• Proficient in CRM tools, ie. Hubspot, Salesforce or other.

Why you should join us:

Looking for a place where your ideas matter, your growth is accelerated, and your work creates real impact? Welcome to Cyara. We're building the assurance layer that gives enterprises the confidence to deploy agentic AI at scale with a global team that values curiosity, collaboration, and continuous learning. Whether you're launching new ideas, solving complex problems, or learning from talented colleagues across the world, you'll be surrounded by people who challenge and support you to do your best work. At Cyara, inclusivity isn't a buzzword, it's part of who we are. We foster a culture where everyone feels seen, heard, and empowered to contribute. Pair that with competitive pay, comprehensive benefits, flexible work options, recognition programs, and a strong focus on employee well-being, and you've got a workplace designed for both success and fulfilment. Big opportunities. Real impact. Amazing people. That's the Cyara experience.

Cyara’s Diversity, Equity, Inclusive and Belonging Statement:

At Cyara, we are dedicated to fostering a workplace that embodies equal opportunity and champions diversity, equity, inclusion, and belonging (DEIB). We strive to cultivate an environment where every individual feels valued, respected, and empowered to bring their whole selves to work, contributing unique perspectives and talents. Our commitment includes continuously evaluating and enhancing our policies, practices, and culture to align with our DEIB principles. We ensure a discrimination‑free environment where individuals are evaluated solely on their merits and abilities, regardless of legally protected statuses such as sex, race, color, ethnicity, national origin, age, religion, disability, sexual orientation, gender identity, veteran status, or medical condition. By celebrating our differences and championing inclusivity, we enrich our organization, make more thoughtful decisions, and drive collective success.

Cyara’s Values Statement:

At Cyara, our values shape everything we do. We're passionate about Delivering Excellence by putting the customer first, collaborating globally, and always striving to improve. We take smart risks and Innovate Boldly, setting new standards and learning from every experience. Integrity First is our cornerstone, we value humility, authenticity, and respect for diversity, building trust in all we do. WeEmbrace Curiosity by empowering you to experiment, learn, and grow in a dynamic environment. At Cyara, our values drive us forward, shaping a culture where innovation and excellence thrive.

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.