Strategic account executive (Central)

WRITER; Chicago (IL); On-site; USD 140,000 - 200,000; Full time

Benefits offered by this job

Generous PTO

Medical, dental, vision coverage

Paid parental leave

Flexible spending account options

Competitive compensation

Company stock options

401k options

Work-life stipends

Company stock options

401k

Company off-sites

Job summary

A tech firm is seeking a strategic sales representative to drive sales in the generative AI space, targeting Fortune 100 and Global 2000 companies. The ideal candidate will have over 8 years of B2B SaaS experience, particularly in closing deals and guiding prospects through business case development. This role offers competitive compensation and comprehensive benefits, including generous PTO and health coverage.

Qualifications

• 8+ years in a B2B SaaS closing role focused on Fortune 100 and Global 2000.
• Experience selling to CIO or AI/innovation leaders preferred.
• Experience with legal, security, and procurement teams.

Responsibilities

• Develop understanding of generative AI space.
• Qualify inbound leads and guide through evaluation.
• Demo to stakeholders and articulate business case.
• Lead champions through budgeting, legal, security, and procurement steps.

Skills

B2B SaaS closing experience

Value-based selling

Strong communication skills

Prospect qualification

Quota attainment

Job description

About this role

We’re looking for a collaborative and builder‑oriented strategic sales rep experienced at helping prospective customers at large companies navigate the evaluation, business case development, and procurement of transformative technology.

Your objective will be to help convert strategic prospects (8k+ FTE) who are active in our trials or who request a sales demo from our website or within our product. While most of your pipeline will come inbound, you'll also be responsible for generating pipeline from ideal customer profile (ICP) accounts within your account set.

Your positivity, sense of curiosity, and ability to create champions from early adopters in the AI space will help shape our entire culture.

You’ll be reporting to our Head of sales.

Your responsibilities

• Develop and maintain a deep understanding of the fast‑moving generative AI space

• Become an expert in the wide range of use cases in which generative AI can drive business transformation for Fortune 100 and Global 2000 enterprises across different industries, and help customers contextualize the pros and cons of our full‑stack approach

• Qualify inbound leads and guide them through the evaluation process

• Generate pipeline from ICP accounts via value‑driven outbounding

• Demo to stakeholders and help prospects articulate and quantify the business case for investment

• Guide prospects through POCs and pilots with clear criteria for success; pull in key stakeholders early and help the team reach Buy consensus

• Lead champions through their internal budgeting, legal, security, and procurement processes (this is an evangelical sale where there is rarely an existing line item for the solution)

• Collaborate with your colleagues to share what is working, what is not, and refine WRITER’s approach to serving strategic customers

Is this you?

• 8+ years in a B2B SaaS closing role focused on Fortune 100 and Global 2000 (15k+ employees); extra points for experience selling to CIO or AI/innovation leaders at Fortune 500 companies.

• Enjoy building in a scrappy, super‑fast‑moving (no, really, we’re not kidding) environment

• Demonstrable, consistent performance, meeting and exceeding quota

• Experience helping prospects build a business case to secure executive sponsorship

• Experience with value‑based selling (but still know the product almost as well as SEs 🤓)

• Experience working with legal, security, and/or procurement teams to win deals

• Strong written and verbal communication skills

• Strong sales process: you are thoughtful about how to make sales repeatable for yourself

Benefits & perks (US Full‑time employees)

• Generous PTO, plus company holidays

• Medical, dental, and vision coverage for you and your family

• Paid parental leave for all parents (12 weeks)

• Fertility and family planning support

• Early‑detection cancer testing through Galleri

• Flexible spending account and dependent FSA options

• Health savings account for eligible plans with company contribution

• Annual work‑life stipends for:

  • Home office setup, cell phone, internet

  • Wellness stipend for gym, massage/chiropractor, personal training, etc.

  • Learning and development stipend

• Company‑wide off‑sites and team off‑sites

• Competitive compensation, company stock options and 401k

WRITER is an equal‑opportunity employer and is committed to diversity. We don’t make hiring or employment decisions based on race, color, religion, creed, gender, national origin, age, disability, veteran status, marital status, pregnancy, sex, gender expression or identity, sexual orientation, citizenship, or any other basis protected by applicable local, state or federal law. Under the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.

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