Go-to-Market Engineer

Awardspring; West Chicago (IL); Hybrid; USD 100,000 - 125,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

401(k) match

Unlimited PTO

Paid parental leave

Job summary

AwardSpring is an established AI-native SaaS company based in Chicago, with a hybrid work model in the West Loop. The Go-to-Market Engineer will empower sellers and CSMs by automating CRM and sales processes to accelerate revenue growth.

Reporting to the Chief AI Officer, you will own top-of-funnel demand generation, pipeline progression, and the enablement of our Customer Success engine, building resilient systems that scale with our multi-tenant platform.

Qualifications

• Technical mindset to design simple, resilient systems.
• Enjoy solving hard, fuzzy problems.
• CRM data design with HubSpot experience preferred.
• Background in RevOps, engineering, growth or sales welcome.

Responsibilities

• Build top-of-funnel discovery, enrichment, and outreach automation.
• Make CRM headless; keep HubSpot updated and clean.
• Automate pipeline progression and MQL-to-SQL handoff.
• Develop Customer Success tooling and renewal cadences.
• Find day-to-day wins from transcripts and data lake; ship daily.

Skills

CRM data design

HubSpot

SaaS enablement

AI tooling

Tools

HubSpot

CRM automation

AI tooling platforms

Job description

• Chicago, West Loop, hybrid three days a week
• AI & Automation

Careers

Go-to-Market Engineer

• Full-Time
• Chicago, West Loop, hybrid three days a week
• AI & Automation

$100,000 - $125,000 base

• $120,000 - $150,000 OTE

~20% variable target

Who we are

AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.

About This Role

The GTM Engineer is responsible for driving revenue growth by enabling our sellers and CSMs to do what they do best: building productive relationships with prospects and customers. Each hour spent building a list, maintaining the CRM record, logging a call, or hunting for the next account is an hour that could be spent with a customer. Your goal is to give them that time back, and the pipeline and revenue that come from more, higher quality meetings.

This is a hands-on building role reporting directly to the Chief AI Officer. You'll start with top-of-funnel demand generation, then extend into pipeline progression and the Customer Success engine, and from there into the systems behind search and answer-engine visibility (SEO/AEO). The Head of Marketing & Demand Gen owns the brand and the message; you build what carries it.

How we work

AwardSpring is an AI-native company. Nearly 100% of the code in our product is AI-generated, and every team here operates on the same principle: routine work gets delegated to AI so people spend their hours on the problems that actually need judgment.

We Hire For Three Things:

• Intellectual curiosity. When you don't know something, you go learn it instead of waiting to be taught.
• Agency. You act without waiting for permission. You take ownership of the problems in front of you and move on them decisively.
• Ambition. You want your work to matter. You are here for real impact, and you are willing to push past your own limits to make it.

We are a small, focused team on a mature, multi-tenant platform. Nobody here has a narrow lane.

What you'll do

• Build the top-of-funnel machine: account and contact discovery, enrichment, intent signals and sequenced outreach, all running autonomously.
• Make our CRM headless. Agents keep HubSpot updated and clean, so no seller maintains a record by hand.
• Automate pipeline progression: lead scoring, routing, follow-up on stalled leads, and the MQL-to-SQL handoff.
• Build the Customer Success engine: account briefs, drafted follow-ups, quotes and service orders drafted for the CSM to check, renewal and cadence tasks, and the adoption signals that tell a CSM who to call next. You work with the Customer Success Lead on what comes off the CSMs' plates next.
• Find the day-to-day wins yourself in call transcripts, Slack conversations and our data lake.
• Ship daily. Then watch it closely, and roll back fast when it's wrong.
• When something you built breaks, fix it or roll it back the same business day.

Who you are

• You work with Claude Code, Codex or similar every day. You're technical enough to design simple, resilient systems, and your agentic process is robust enough that you don't need to read the code you ship.
• You're energized by a hard, fuzzy problem. "Sellers lose half their day to software admin" is a problem you want, and you start building before anyone asks.
• You know CRM data design well (ideally HubSpot), and inconsistent, messy data is one of your pet peeves.
• RevOps, engineering, growth or sales backgrounds all work. We care about what you've built, not where you trained.

What we're not looking for

• Someone who waits for a ticket. If you need a spec handed to you before you start, this is the wrong seat.
• Someone who configures instead of builds. We aren't hiring a HubSpot admin with a new title.

How we'll measure you

• Customer meeting hours per Account Executive and CSM, per week. The most direct way your work enables the team.
• Pipeline dollars generated each month across new business, cross-sell and upsell. Shared with every seller on purpose: the machine you build is only worth the pipeline it helps create.
• Net GTM efficiency. Net new recurring revenue in the quarter, after churn and downgrades, against sales, marketing and customer success cost. Your machines make every dollar of revenue cheaper to win and to keep.

On the AI part of this job

Unlike most roles here, we won't teach you to work AI-native. You arrive fluent: directing agents is already how you build, every day. We check in at day 30 on how you're working, not only on what you've shipped.

How you advance

Growth here doesn't require a management ladder. Strong GTM Engineers will slowly but steadily be given more autonomy, more scope, and ownership of higher-level KPIs. If you're looking for career progression into a people management track, this likely isn't the role for you.

What we give you

• Top-tier AI tooling with unlimited token budgets
• Day-one access to the latest models as they ship
• A mature, multi-tenant production codebase with real users and real stakes
• Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave

Our values

Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.

Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.

Take pride in the process. Fast is the standard and thoughtfulness is non-negotiable. Eyes on the work you control, not the scoreboard.

Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.

Work location

Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week. In-office presence is part of the job, with the specific schedule set with your manager.

How we hire

• A conversation with our CEO.
• A short take-home: build something small with AI, then walk us through how you built it.
• Interviews with the team you would work with.
• A second, longer take-home.
• A final debrief and an offer.

AI in hiring

We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. Prefer a review without AI assistance? Email our hiring team at [e-mail] to request it. It will not disadvantage you.

Equal Opportunity Employer

AwardSpring is an equal opportunity employer and hires without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. We're committed to an inclusive, harassment-free workplace.

Who we are

AwardSpring is an established, growing SaaS company that partners with hundreds of colleges, universities, and foundations across the US and Canada to award scholarships and manage their donors. We complete the virtuous cycle of giving, getting, and giving again, on a mature, multi-tenant platform, with a small, focused team.

We Hire For Three Things:

• Intellectual curiosity. When you don't know something, you go learn it instead of waiting to be taught.
• Agency. You act without waiting for permission. You take ownership of the problems in front of you and move on them decisively.
• Ambition. You want your work to matter. You are here for real impact, and you are willing to push past your own limits to make it.

We are a small, focused team on a mature, multi-tenant platform. Nobody here has a narrow lane.

What you'll do

• Build the top-of-funnel machine: account and contact discovery, enrichment, intent signals and sequenced outreach, all running autonomously.
• Make our CRM headless. Agents keep HubSpot updated and clean, so no seller maintains a record by hand.
• Automate pipeline progression: lead scoring, routing, follow-up on stalled leads, and the MQL-to-SQL handoff.
• Build the Customer Success engine: account briefs, drafted follow-ups, quotes and service orders drafted for the CSM to check, renewal and cadence tasks, and the adoption signals that tell a CSM who to call next. You work with the Customer Success Lead on what comes off the CSMs' plates next.
• Find the day-to-day wins yourself in call transcripts, Slack conversations and our data lake.
• Ship daily. Then watch it closely, and roll back fast when it's wrong.
• When something you built breaks, fix it or roll it back the same business day.

Who you are

• You work with Claude Code, Codex or similar every day. You're technical enough to design simple, resilient systems, and your agentic process is robust enough that you don't need to read the code you ship.
• You're energized by a hard, fuzzy problem. "Sellers lose half their day to software admin" is a problem you want, and you start building before anyone asks.
• You know CRM data design well (ideally HubSpot), and inconsistent, messy data is one of your pet peeves.
• RevOps, engineering, growth or sales backgrounds all work. We care about what you've built, not where you trained.

What we're not looking for

• Someone who waits for a ticket. If you need a spec handed to you before you start, this is the wrong seat.
• Someone who configures instead of builds. We aren't hiring a HubSpot admin with a new title.

How we'll measure you

• Customer meeting hours per Account Executive and CSM, per week. The most direct way your work enables the team.
• Pipeline dollars generated each month across new business, cross-sell and upsell. Shared with every seller on purpose: the machine you build is only worth the pipeline it helps create.
• Net GTM efficiency. Net new recurring revenue in the quarter, after churn and downgrades, against sales, marketing and customer success cost. Your machines make every dollar of revenue cheaper to win and to keep.

On the AI part of this job

Unlike most roles here, we won't teach you to work AI-native. You arrive fluent: directing agents is already how you build, every day. We check in at day 30 on how you're working, not only on what you've shipped.

How you advance

Growth here doesn't require a management ladder. Strong GTM Engineers will slowly but steadily be given more autonomy, more scope, and ownership of higher-level KPIs. If you're looking for career progression into a people management track, this likely isn't the role for you.

What we give you

• Top-tier AI tooling with unlimited token budgets
• Day-one access to the latest models as they ship
• A mature, multi-tenant production codebase with real users and real stakes
• Health, dental, and vision insurance, 401(k) match, unlimited PTO, and paid parental leave

Our values

Lead with humanity. Genuine empathy for our team, our customers, and the students and donors they serve. That includes candor, saying the hard thing because you respect the person enough to say it.

Take smart risks. Urgency. Bold, informed bets before the picture is fully clear. Run the experiment instead of winning the debate.

Take pride in the process. Fast is the standard and thoughtfulness is non-negotiable. Eyes on the work you control, not the scoreboard.

Own the results. We measure everything. Accountability runs on data, not vibes, and we can tell the difference between an honest miss and a broken process.

Work location

Hybrid, based in our West Loop / Fulton Market office in Chicago, three days a week. In-office presence is part of the job, with the specific schedule set with your manager.

How we hire

• A conversation with our CEO.
• A short take-home: build something small with AI, then walk us through how you built it.
• Interviews with the team you would work with.
• A second, longer take-home.
• A final debrief and an offer.

AI in hiring

We use AI tools to assist in screening applications and assessing fit. Final hiring decisions are made by humans. Prefer a review without AI assistance? Email our hiring team at [e-mail] to request it. It will not disadvantage you.

Equal Opportunity Employer

AwardSpring is an equal opportunity employer and hires without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. We're committed to an inclusive, harassment-free workplace.