Senior Account Executive (New Business)

Askable; Chicago (IL); On-site; USD 80,000 - 120,000; Full time

Benefits offered by this job

Competitive Salary with Commission

Generous Paid Time Off

Health Insurance

401k Matching

Additional 'Askable Days'

Job summary

Askable is looking for a Senior Account Executive based in Chicago to enhance client relationships and drive sales. This role involves identifying new business opportunities, managing complex sales processes, and collaborating with product and marketing teams. Ideal candidates will have at least three years of SaaS sales experience and a proven ability to close large deals. Perks include competitive salary, generous paid time off, and health insurance.

Qualifications

• At least 3 years of experience in SaaS sales with a strong track record.
• Experience in closing large, complex software deals.
• Proven relationship-building skills with customers.

Responsibilities

• Drive revenue by exceeding sales targets through effective sales strategies.
• Identify and source new prospects while nurturing existing accounts.
• Deliver product demonstrations and tailored solutions to clients.

Skills

SaaS sales experience

Relationship Building

Sales Forecasting

Solution Selling

Tools

Hubspot

LinkedIn Sales Navigator

Lemlist

Job description

Heads up! This role is based in-person at our office in Chicago.

About Askable

Hey, we’re Askable - the world’s most loved user research platform. Loved by whom, you ask? Mastercard, Toyota, McDonalds, Canva and hundreds more. Not bad right?

Askable began in 2017 as an idea scribbled on a sticky note, born out of frustration with the clunky, outdated research processes we’d experienced firsthand. So, we set out to build a new way — one that makes quality research accessible to everyone, from Fortune 500s to startups hungry for insights.

Today, Askable brings together everything teams need to run research end-to-end: seamless access to high-quality participants, Certified Askable Researchers, and an expanding AI suite that helps teams move faster — from turning raw feedback into clear insights, to streamlining workflows and elevating research quality at scale.

By combining expert-led research services with powerful software (and now AI), we enable teams to scale research on demand, deliver insights faster, and ultimately build things that matter.

Now with offices in Brisbane, London, and Chicago, we’re growing the team to bring Askable’s research power to teams everywhere, so they can make smarter, user-driven decisions.

Our culture

Our culture drives everything we do. We live it, breathe it, and work every day to make Askable a place where people can thrive.

We believe work should be fulfilling, exciting, and meaningful. Here, you’re not just part of a team. You’re part of a community that cares about what they’re building and how they’re building it.

In fact, we take culture so seriously that we wrote a book on it. Our Culture Book guides what we stand for, how we work, and the values that unite us—because nothing beats winning with a team you genuinely love working with. (Ask for a copy!)

About the role

As a Senior Account Executive you’ll find and close organizations (that we’re not yet working with) who want to gain a deeper, up-to-date understanding of their customers.

You’ll work closely with our product, marketing and customer success teams to understand all facets of customer research, user testing and how our research platform helps collect real-world customer feedback and turn it into actionable insights.

Armed with this knowledge you’ll build deep, trusted relationships with prospects, navigate complex enterprise procurement processes and exceed your sales quota to drive business growth.

You’ll be based in our Chicago office but with frequent travel to meet your customers in-person (new and existing). Yes, you will get to fly to regions across the US on the regular (every 4-6 weeks) - hello frequent flyer points!

What you’ll do

• Drive Revenue: Consistently surpass annual targets by navigating a complex, solution-focused sales process that engages multiple stakeholders and departments across large enterprises.

• Lead Sourcing: In addition to following up on supplied leads you’ll use your outreach/hunting skills to proactively identify new prospects and create opportunities for yourself.

• Product Demonstrations and Custom Solutions: Deliver compelling demonstrations to new teams in existing accounts and create custom solutions tailored to unique client needs.

• 360 Responsibility: Drive the entire sales journey—from building a healthy pipeline and following up on leads, through qualifying opportunities, presenting proposals, closing deals, and maintaining relationships for long-term retention.

• Sales Forecasting: Confidently forecast sales opportunities with accuracy, tracking the key metrics that truly predict success.

• Utilize Our Sales Platforms: including Hubspot, LinkedIn Sales Navigator, Lemlist and others to manage and grow business efficiently.

You’ll also:

• Attend industry events to build in person connections.

• Work with our Events Manager to conceptualize, plan, invite attendees and run our own events

• Travel to meet with prospects at their offices

In short… Your mission is to drive pipeline growth and boost revenue

Skills and experience you’ll bring

To hit the ground running in this role you’ll need at least 3 years experience winning net-new logos with a strong track record of success in SaaS sales.

Ideally, you’ll have experience:

• Closing large, complex software deals across multi-layered businesses and diverse industries, effortlessly navigate multiple stakeholders from individual contributor to senior leadership.

• Building meaningful relationships with customers, gaining authentic trust by deeply understanding business problems and opportunities and bringing real value with your proposed solutions.

• Confidently using creative levers and compelling incentives to drive opportunities to close within a fiscal period.

• Utilizing sales methodologies like the The Challenger Sale and The Sales Acceleration Formula.

The mindset you’ll need

• Winning with your team: You’ll be proud of the individual work you do, but find winning as team ultimately more fulfilling. This includes having the emotional maturity to give and receive constructive feedback to better the team as a whole.

• Independence and curiosity: You won’t find cabinets full of step by step instructions at Askable. You’ll need to think on your feet, manage your own workflow, problem-solve roadblocks, proactively ask questions, and take responsibility for the goals you set.

• Growth focussed: You’ll enjoy the idea of a stretch goal and always be looking for opportunities to improve yourself, your team, and the business.

• Quick to learn: You’ll bring an ability to quickly learn and understand our product solutions and features, and keep up to date as our offerings evolve.

Perks and benefits

Competitive Salary (plus commission and bonuses based on performance)

Generous Paid Time Off (plus extra ‘Askable Days’ – a full day off just for you each month)

Great Health Insurance

401k Matching

Plus much more!... we'll be happy to talk about the rest during the interview process...

Before you go...

Research shows many people (especially women and minority groups) hesitate to apply unless they meet every single requirement. At Askable, we’re committed to building diverse teams with unique perspectives. If you’re excited about this role but your experience doesn’t align perfectly, we’d still love to hear from you.