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About the Role

As an Account Executive, you’ll be on the front lines of Siena’s growth, closing high-value enterprise deals and bringing AI-driven automation to the world’s top brands. This role is built for a hunter, someone who thrives in prospecting, navigating complex sales cycles, and turning cold leads into long-term partnerships. If you have experience selling into enterprise CX, or AI-driven automation, this is an opportunity to shape the future with Siena.

Responsibilities

Own the full sales cycle from prospecting to close, targeting enterprise accounts.
Build and maintain strong relationships with senior decision-makers in CX, digital transformation, and operations.
Develop strategic outbound motions to break into top accounts and expand Siena’s footprint.
Manage complex, multi-stakeholder sales cycles with a consultative and value-driven approach.
Work closely with marketing, sales development, and solutions engineering to refine our go-to-market strategy.
Drive adoption of Siena’s AI solutions by aligning our capabilities with customer pain points and business outcomes.
Consistently exceed quota and revenue targets, contributing to Siena’s high-growth trajectory.
Leverage AI tools to scale prospecting, research, and deal preparation.
Build and maintain custom AI workflows for account intelligence, objection handling, and competitive analysis.

Requirements

5+ years of experience in enterprise SaaS sales, ideally in AI, CX, automation technology.
Proven success in hunting new business and closing six- and seven-figure deals.
Skilled in multi-threading enterprise sales cycles and navigating complex organizations.
Deep understanding of enterprise customer experience, digital transformation, and automation trends.
Highly strategic and data-driven, leveraging insights to optimize deal execution.
Comfortable working in a fast-moving startup environment where adaptability and ownership are key.
Power-user of AI tools with proven ability to build custom agents/prompts that enhance sales productivity.
Comfort with rapidly evolving AI landscape by staying current on AI capabilities and applying them to sales motion.
Experience selling AI, automation, or workflow intelligence products.
Established relationships within executives, CX, eCommerce, or BPOs.
Experience selling enterprise and multi-product software.

Skills

AI
CX
Automation technology
Enterprise SaaS sales
Prospecting
Sales cycle management
Relationship building
Outbound sales
Consultative selling
Value-driven sales
Go-to-market strategy
AI solutions
Customer pain points
Business outcomes
Quota attainment
Revenue targets
AI tools
Account intelligence
Objection handling
Competitive analysis
AI-driven automation
Digital transformation
Data-driven decision making
Adaptability
Ownership
AI workflow development
Sales productivity enhancement
AI capabilities application
Ecosystem of agents
Research
Debugging
Writing
Analysis
Writing code

Location

Work Type

Hybrid

Experience Level

5+ years of experience in enterprise SaaS sales

Salary/Compensations

Great salary plus equity or stock grants

Benefits

Real ownership
Autonomy to solve problems
Trust to work without micromanagement
Work that ships and matters
Category creation
Team that respects judgment
Globally distributed team
Async-first approach
Low bureaucracy
Equity or stock grants
Learning budget
AI-fluency by default
Premium AI accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable)
Quarterly budget for new AI tools

About the Company

Siena is the Agent of Record for consumer brands.
One agent that owns the entire customer journey, running on a shared intelligence layer no point tool can replicate.
Consumer brands run ten or more disconnected tools to manage their customers. Siena collapses that stack into a single agent.
It started with support, the hardest surface a brand has, and it expands from there: Shopping Agent, Social Agent, Siena working alongside a brand's own operators.
One agent across every surface, with shared memory, shared context, and shared tools.
Hundreds of brands already run real customer volume on Siena in production.
This is built, working, and growing, and we are racing to build what comes next.
We are a small, fully distributed, global team.
We have built leverage into how we work, which is what lets a team this size move at the speed we do.
We hire athletes. Everyone here owns real outcomes, defaults to writing over meetings, communicates with directness, and acts the moment they see something worth acting on.
Low ego, high standards, fast clock.
The Agent of Record is new ground, with unsolved problems and cutting-edge models, not a crowded field to compete in.
We hire adults and treat you like one.
The people who thrive here are curious, customer-obsessed, and take ownership without being asked.
They fix problems first and explain later.
They're direct about feedback—both giving and receiving it—because they care more about getting things right than being polite.
They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that's how great work gets done.
When things get tough, they adapt and keep pushing forward.
The people who thrive here treat AI like a natural extension of themselves.
They've built their own ecosystem of agents - some for research, others for debugging, writing, analysis, or writing code.
They know which AI works best for what problem.
We're not just looking for people who can do a job.
We’re looking for people who want to break boundaries, create the future, and reshape industries.

Equal Opportunity

Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression.
We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.
We use AI-assisted screening tools as part of our hiring process. All decisions are made by humans. You can request a human-only review at talent@siena.cx.