Jobs at Sierra

Own full-cycle recruiting for technical, sales, go-to-market, and corporate roles. Partner with hiring managers to define roles, set priorities, assess talent markets, develop sourcing strategies, evaluate candidates, and close senior hires. Track recruiting metrics and report insights to leadership. The role requires strong networks among technical, corporate, or sales talent in Japan, excellent English and Japanese communication skills, and experience recruiting at high-growth technology companies.

Lead enterprise sales growth across the Benelux by prospecting, building executive relationships, managing complex negotiations, closing large accounts, and developing regional sales strategies. As the first regional salesperson, this role will help establish Sierra’s go-to-market motion while collaborating with marketing, product, technical, operations, legal, and finance teams.

Own sales compensation communications, plan launches, policy updates, rep support, training, and enablement. Model plan costs, payouts, and behavioral impacts; support annual plan design and monthly commission payroll through payout validation, reconciliation, and payroll handoff. Use Salesforce and compensation tools to report attainment and payouts while coordinating plan changes across systems and processes.

Own the full lifecycle of sales plays, from intake and prioritization through development, launch, seller training, measurement, and retirement. Partner with Product Marketing, Product, Sales Leadership, and Sales Engineering to create messaging, demos, battlecards, objection handling, and proof points. Measure play adoption and business impact, report results, and adapt programs for regional teams.

Build and optimize recruiting processes, interview workflows, dashboards, and AI-enabled tooling. Manage and customize the Ashby ATS and related recruiting systems, identify operational bottlenecks, improve hiring practices, and support interviewer enablement through training and documentation. Partner with recruiters, hiring managers, and cross-functional stakeholders in a fast-paced technology environment.

Conduct an applied AI research project with mentorship, covering agent evaluation, reasoning, tool use, policy adherence, post-training, and multimodal or voice models. Design rigorous experiments, analyze proprietary text and audio datasets, develop benchmarks, write and submit research papers, and collaborate with engineers to translate findings into production improvements.

Manage the operating cadence for Product and Engineering incident response teams, including planning, sprint workflows, retrospectives, dashboards, and initiative tracking. Coordinate cross-functional initiatives across Product, Engineering, Legal, Security, and Operations. Build scalable execution frameworks, analyze operational data, identify friction points, and improve processes, alignment, and team outcomes.

Support sales, marketing, and customer-facing teams by optimizing go-to-market processes, territories, pricing, campaigns, and customer presentations. Analyze data, build financial models, develop executive recommendations, and lead strategic initiatives across pricing, legal, finance, and international expansion. Use AI-native tools to automate workflows and create internal systems that improve revenue operations.

Own the technical pre-sales process for enterprise financial services customers, partnering with sales teams to discover use cases, design and demonstrate AI agent solutions, lead architecture and technical reviews, and communicate business value. Build tailored working agents, support procurement and executive stakeholders, mentor sales engineers, contribute reusable assets, and remain involved through implementation, launch, and account expansion.

Own the technical pre-sales process for large financial services customers, partnering with sales teams to scope use cases, design and demo AI solutions, lead architecture and technical reviews, communicate business value, and support deals through launch and expansion. Build tailored working agents, engage executives and technical stakeholders, mentor sales engineers, create reusable assets, and apply AI tools to discovery, solution design, prototypes, and proposals.

Lead sales enablement across EMEA by designing onboarding, training, AI adoption, sales plays, and coaching programs for sales and sales engineering teams. Train teams on AI tools, GDPR, and the EU AI Act; create playbooks and workflows; measure adoption, productivity, ramp speed, and deal velocity; localize global programs; report results to leadership; and develop the regional enablement team, including future hiring and people management.

Own end-to-end technical programs for enterprise AI deployments in customer-owned cloud environments. Coordinate infrastructure, security, networking, provisioning, model access, and observability teams; manage milestones, dependencies, risks, escalations, and launch cadence. Translate technical requirements into actionable plans and improve Sierra’s deployment playbooks, tooling, and operating standards while establishing the infrastructure TPM function.

Provides strategic and administrative support to the General Counsel and Partnerships leaders by managing calendars, travel, meetings, correspondence, events, and confidential information. Coordinates meeting preparation and follow-up, builds relationships with internal and external stakeholders, negotiates travel-related contracts, and develops administrative systems for a growing startup. The role requires regular in-office work in San Francisco and occasional travel with executives.

Design, build, and operate multi-cloud infrastructure across AWS, GCP, and Azure using Terraform and Kubernetes. Standardize deployments, support multi-tenant and isolated customer environments, build security and compliance guardrails, improve release tooling, and operate FedRAMP infrastructure. Drive reliability through observability, incident response, root cause analysis, and postmortems while writing Go-based automation and partnering with BYOC teams.

Own end-to-end technical pre-sales for strategic enterprise accounts, including discovery, solution design, demonstrations, architecture and security reviews, technical proposals, and executive stakeholder engagement. Mentor Sales Engineers, establish strategic deal playbooks, support customer launches and expansion, and share account insights with Product leadership. The role requires experience selling complex AI or technical products, leading $1M+ deals, and partnering with enterprise architects, engineering, and security teams.

Own strategic enterprise technical sales for financial services accounts, from discovery and solution design through demos, architecture and security reviews, deal closure, launch, and expansion. Build trusted executive relationships, lead $1M+ sales processes, coordinate internal teams, mentor sales engineers, create strategic deal playbooks, and inform product roadmaps. Apply AI tools to prepare discoveries, prototypes, demos, and proposals while ensuring customer-facing accuracy.

Own the technical pre-sales process for enterprise customers, from discovery and solution design through demos, architecture reviews, proposals, and deal close. Build tailored AI agent prototypes, explain business and technical value, collaborate with CX, IT, security, procurement, and executives, and support account expansion after the sale. Mentor sales engineers, create reusable assets, and use AI tools to improve technical sales workflows.

Owns strategic enterprise technical sales for financial services accounts, including discovery, solution design, demos, architecture and security reviews, technical proposals, and customer expansion. Builds executive and technical relationships, leads cross-functional deal execution, mentors sales engineers, develops strategic sales playbooks, supports post-sale launches, and informs product roadmap. The role focuses on selling Sierra’s AI agent platform to major financial institutions.

Own the end-to-end technical pre-sales process for strategic enterprise accounts, including discovery, solution design, demos, architecture and security reviews, technical proposals, and customer presentations. Build executive and technical relationships, support launches and account expansion, mentor sales engineers, develop strategic-deal playbooks, coordinate internal teams, and communicate customer insights to Product leadership. The role requires selling complex AI products to customers with $1M+ deal sizes.

Partners with enterprise sales teams to win and expand financial services customers. Leads the technical pre-sales cycle, including discovery, solution scoping, business-value articulation, platform design, demonstrations, architecture reviews, prototypes, and technical proposals. Collaborates with Sales, Product, and Agent Engineering to improve customer solutions and scale successful industry motions.