About this role.
Sierra is seeking a highly experienced Sales Director who is fluent in both Brazilian Portuguese and English to drive enterprise sales in a fast-growing AI customer experience platform. The role involves full-cycle sales, from prospecting and lead generation to negotiating and closing complex deals of $1M+ ACV. The director will also shape the go-to-market strategy, working cross-functionally with product, marketing, and operations teams. This is a senior, high-impact position that requires deep enterprise relationships and a track record of exceeding sales quotas. Based in San Francisco, the company values trust, customer obsession, craftsmanship, intensity, and family.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Cover letter sample
Dear Hiring Manager,
I am writing to express my strong interest in the Sales Director position at Sierra. With over 10 years of enterprise sales experience, including managing $1M+ quotas and closing complex 6- and 7-figure deals, I am confident in my ability to drive significant revenue growth and help shape your go-to-market strategy. I am fluent in both Brazilian Portuguese and English, enabling me to build authentic relationships with diverse stakeholders across the Americas and beyond.
My background includes leading full-cycle sales, from prospecting to negotiation, and collaborating with product and marketing teams to deliver tailored solutions. I am particularly drawn to Sierra's mission of creating more human AI experiences, and I am excited by the opportunity to work with a world-class team to redefine customer experience.
Thank you for your consideration. I look forward to the opportunity to contribute to Sierra's success.
Sincerely,
[Your Name]
Sample interview questions
I have consistently exceeded quotas by focusing on a disciplined pipeline management approach, identifying high-value accounts with clear pain points, and building strong executive relationships. I apply a consultative sales methodology, leverage data to prioritize opportunities, and align internal resources to drive deals to closure. For example, in my previous role, I exceeded my $1.2M quota by 15% for three consecutive years through strategic territory planning and cross-functional teamwork.
I would start by deeply understanding our target customer, market landscape, and the unique value of the AI platform. From there, I would define an ideal customer profile, develop a repeatable sales process, and establish metrics for pipeline generation and conversion. I would also collaborate with marketing to create campaigns and with product to ensure our positioning resonates. Building a high-performing team would involve hiring for both skill and cultural fit, while implementing training and enablement programs.
In a complex $1.5M enterprise deal, I worked closely with legal to address contractual risks, finance to structure payment terms, and procurement to streamline the vendor evaluation process. I maintained clear communication among all parties, anticipated objections, and built a business case that highlighted ROI for the customer. By fostering a collaborative environment and focusing on mutual value, I was able to close the deal within the expected timeline.
My fluency allows me to communicate directly with key decision-makers in their native language, which accelerates trust and credibility. I would target multinational companies with headquarters or branches in Brazil, as well as local enterprises that align with our customer profile. I would also use my understanding of local business culture to tailor messaging and navigate different negotiation styles, ensuring a smoother path to closure.
I regularly follow industry publications, attend conferences, and participate in professional networks focused on AI and enterprise technology. This knowledge helps me speak intelligently about how AI can solve customer pain points and anticipate market shifts. In sales strategy, I use these insights to position our product as a forward-looking solution, create relevant content for prospects, and advise customers on emerging use cases.
About us
At Sierra, we’re creating a platform to help businesses build better, more human customer experiences with AI. We are primarily an in-person company based in San Francisco, with growing offices in Atlanta, New York, London, Paris, Madrid, Munich, Singapore, Tokyo, and Sydney.
We are guided by a set of values that are at the core of our actions and define our culture: Trust, Customer Obsession, Craftsmanship, Intensity, and Family. These values are the foundation of our work, and we are committed to upholding them in everything we do.
Our co-founders are Bret Taylor and Clay Bavor. Bret currently serves as Board Chair of OpenAI. Previously, he was co-CEO of Salesforce (which had acquired the company he founded, Quip) and CTO of Facebook. Bret was also one of Google’s earliest product managers and co-creator of Google Maps. Before founding Sierra, Clay spent 18 years at Google, where he most recently led Google Labs. Earlier, he started and led Google’s AR/VR effort, Project Starline, and Google Lens. Before that, Clay led the product and design teams for Google Workspace.
What you’ll do
Prospecting & lead generation: Identify and target potential customers through research, networking, and cold calling. Build new relationships with our enterprise customers and prospects to drive revenue, pipeline, and deployment capacity.
Manage relationships: Build and maintain strong relationships with key decision-makers and stakeholders with our largest customers. Serve as their primary point of contact and exceed their expectations.
Negotiating & closing complex deal cycles: Lead negotiations with existing and prospective customers, addressing objections and closing deals. Navigate contracts and agreements quickly and effectively, working closely with legal and finance stakeholders.
Sales strategy & planning: Develop and execute sales strategies to meet or exceed sales targets. Craft tailored sales presentations and proposals that meet our enterprise customers needs. Collaborate with our marketing team to implement effective sales campaigns and presentations.
Help define our sales motion: We’re an early team, and your work will directly impact how our GTM function operates and succeeds.
Collaborate cross-functionally: Work closely with our broader GTM team, as well as our product, technical and operations orgs to deliver our industry-leading product.
What you’ll bring
Language fluency: professional fluency in both Brazilian Portuguese and English
8-12+ years of experience in an enterprise customer-facing sales role, identifying and closing large accounts.
Enterprise experience: Experience managing a $1M+ quota, and running end-to-end complex 6- and 7-figure ACV deals.
Strong communication skills: Exceptional verbal and written communication abilities.
Analytical mindset: Ability to analyze market trends, identify opportunities, and make data-driven decisions.
Prospecting & lead generation: Proven track record of identifying and targeting potential enterprise clients through research, networking, and cold calling.
Even better…
Industry knowledge: Familiarity with the AI landscape, key players, and emerging trends.
Experience building GTM strategies: Building sales teams and sales motions from scratch, or from early stage growth.
Our values
Trust: We build trust with our customers with our accountability, empathy, quality, and responsiveness. We build trust in AI by making it more accessible, safe, and useful. We build trust with each other by showing up for each other professionally and personally, creating an environment that enables all of us to do our best work.
Customer Obsession: We deeply understand our customers’ business goals and relentlessly focus on driving outcomes, not just technical milestones. Everyone at the company knows and spends time with our customers. When our customer is having an issue, we drop everything and fix it.
Craftsmanship: We get the details right, from the words on the page to the system architecture. We have good taste. When we notice something isn’t right, we take the time to fix it. We are proud of the products we produce. We continuously self-reflect to continuously self-improve.
Intensity: We know we don’t have the luxury of patience. We play to win. We care about our product being the best, and when it isn’t, we fix it. When we fail, we talk about it openly and without blame so we succeed the next time.
Family: We know that balance and intensity are compatible, and we model it in our actions and processes. We are the best technology company for parents. We support and respect each other and celebrate each other’s personal and professional achievements.
What we offer
We want our benefits to reflect our values and offer the following to full-time employees:
Flexible (unlimited) paid time off
Medical, dental, and vision benefits for you and your family
Life insurance and disability benefits
Retirement plan dependent on country of employment
Parental leave
Fertility and family building benefits through Carrot
Lunch, as well as delicious snacks and coffee to keep you energized
Discretionary benefit stipend giving people the ability to spend where it matters most
Free alphorn lessons
These benefits are further detailed in Sierra’s policies, may vary by region, and are subject to change at any time, consistent with the terms of any applicable compensation or benefits plans. Eligible full-time employees can participate in Sierra’s equity plans subject to the terms of the applicable plans and policies.
Be you, with us
We’re working to bring the transformative power of AI to every organization in the world. To do so, it is important to us that the diversity of our employees represents the diversity of our customers. We believe that our work and culture are better when we encourage, support, and respect different skills and experiences represented within our team. We encourage you to apply even if your experience doesn’t precisely match the job description. We strive to evaluate all applicants consistently without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class.
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