Geared toward enterprise software sales professionals comfortable with technical sales and product collaboration, this role is based in San Francisco and requires defining new processes in a fast-growing startup environment.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Outset via Ashby
Outset invented a better way to do research: AI-powered user interviews.
Global brands like Hubspot, Microsoft, Uber and Nestle use Outset to achieve deeper, qualitative insights about their users at unprecedented speed and scale.
The research industry is massive (>$140B and growing) and ripe for disruption. Incumbents are outdated, slow, and burdened by high-cost services. That's our opportunity.
Outset is backed by top Silicon Valley investors and raised a $30M Series B in December 2025—less than six months after our Series A—led by Radical Ventures with participation from M12 (Microsoft’s venture arm), 8VC, Y Combinator, and Adverb Ventures.
The raise follows a breakout year, with our business growing 8x as enterprise customers across industries adopt our category, AI‑moderated research, as the new standard for understanding people.
We’re a tight-knit team serving some of the world’s largest enterprises.
Outset is hiring its founding Customer Experience (CX) Solutions Account Executive, the first sales hire for our new CX offering.
On Day 1, you'll own the most important stretch of the funnel, discovery → demo → pilot → conversion, working directly with prospects and turning interest into paying customers.
When another Account Executive is on the deal, you'll partner with them as the solution lead. When one isn't, you'll run the full cycle as both AE and SC. Most critically, you'll work hand in hand with Product: bringing customer feedback that shapes and delivers the short-term roadmap, and translating that roadmap into a sellable medium- and long-term vision for clients.
As the founding hire, you'll define how CX is sold at Outset.
Responsibilities
Own discovery → demo → pilot → conversion
- Discovery: Lead discovery with CX leaders and technical stakeholders to uncover program goals, pain points, buying process, and current stack (Medallia, Qualtrics, CRM, support, and data platforms).
- Demo: Build and deliver tailored demos that map the CX offering to each prospect's use cases; continuously refine the demo narrative, environments, and datasets.
- Pilot: Scope pilots with clear success criteria, timelines, and stakeholders; stand up the integrations (APIs, MCP, data connections) and drive each pilot to a decision.
- Conversion: Turn successful pilots into paid contracts by building the business case, tying results to outcomes, and navigating procurement and security review.
- Track conversion at each stage (discovery to demo, demo to pilot, pilot to close) and iterate on what works.
Own deals end to end
- When another AE is on the deal, partner with them as the solution lead, co-owning deal strategy and the technical path to close.
- Otherwise, run the full cycle as both AE and SC: own pipeline, forecasting, commercial negotiation, and close.
- Hand off cleanly to Customer Success and stay involved through onboarding and early value realization.
Partner with Product and sell the vision
- Be the voice of the CX customer inside Product, bringing structured, prioritized feedback from discovery, demos, and pilots to shape the short-term roadmap.
- Work hands-on with Product and Engineering to validate and deliver near-term roadmap items with pilot customers and design partners.
- Translate the roadmap into a compelling medium- and long-term vision that clients can buy into, while keeping commitments credible.
- Spot patterns across deals (integration gaps, feature requests, competitive objections) and feed them into product and positioning.
Build the function
- Create the CX sales playbook: discovery guides, demo scripts, pilot templates, business case models, and integration reference architectures.
- Define the processes and metrics for CX sales and help shape future hiring.
Qualifications
- 6+ years of hands-on experience in the enterprise software sales space, such as sales development representative, account executive, solutions consulting, sales engineering.
- 2+ years working specifically with customer experience solutions.
- A track record in a customer-facing pre-sales role, owning and delivering discovery, demos, and pilots or proofs of concept that converted to revenue.
- A track record of closing deals end to end, including pipeline management, business case, commercial negotiation, and close.
- Experience partnering closely with Product teams, turning customer input into roadmap priorities and selling a credible product vision.
- Working familiarity with Medallia and/or Qualtrics, including how they are deployed, configured, and connected to other systems.
- Demonstrated experience building and supporting a variety of data integrations, including REST APIs, webhooks, authentication methods (OAuth, API keys), and data mapping.
- Experience with, or strong working knowledge of, Model Context Protocol (MCP) and how it connects AI tools to external systems.
- Clear written and verbal communication, with the ability to explain technical concepts in terms of business value to technical and executive audiences.
- A founder's mindset: comfortable being first in a role and creating structure where none exists.
Bonus
- Integration experience with some combination of the following:
- CRM platforms (e.g., Salesforce, HubSpot)
- Customer Success platforms (e.g., Gainsight, Totango, ChurnZero)
- Customer Support platforms (e.g., Zendesk, Intercom, Salesforce Service Cloud)
- Data lakes and warehouses (e.g., Snowflake, Databricks, BigQuery)
- Quota-carrying experience in a combined AE and SC (or technical seller) role.
- Experience as a founding or first sales hire for a new product line or at an early-stage company.
- Familiarity with CX program concepts such as voice of the customer (VoC), NPS/CSAT/CES, journey analytics, and closed-loop feedback.
- Scripting or light development skills (e.g., Python, JavaScript, SQL) for building prototypes and demo tooling.
- Experience with ETL/reverse-ETL tools or iPaaS platforms (e.g., Fivetran, Census, Workato, MuleSoft).
- Background with AI-powered or research products.
Source: Outset careers (Ashby)