Strategic CSM: Adoption & Renewal Leader

Awardspring; Chicago (IL); Hybrid; USD 70,000 - 110,000; Full time

Benefits offered by this job

Health insurance

Dental insurance

Vision insurance

401(k) match

Unlimited PTO

Parental leave

Job summary

AwardSpring is seeking a Customer Success Manager in Chicago to own customer health from onboarding to renewal and upsell. You will be the single point of contact, resolving requests, routing to Support/Product/AE, and escalating early when risk appears.

You will drive renewals, upsell add-ons, and run workshops to increase product adoption, with a strong emphasis on proactive communication and CRM hygiene in HubSpot. This hybrid role is based in Chicago with a mature, AI-enabled product suite.

Qualifications

• 2+ years in customer success or account management at a SaaS company.
• Ability to own renewals, upsell, and manage accounts end to end.
• Strong listening and questioning to understand customer needs and drive outcomes.

Responsibilities

• Spend 60% of your week with customers in live meetings, workshops, and best-practice sessions.
• Maintain tiered cadence: quarterly/monthly touchpoints per tier.
• Prepare for each meeting with a clear brief and objectives.
• After meetings, send a written recap with next steps within 24 hours and log it in HubSpot.
• Respond to customer emails within 4 business hours.
• Kick off renewals at least 6 months before contract end and issue service orders 60 days prior to auto-renewal deadlines.
• Own renewal and upsell from quote to signature, including terms and context for cross-sell opportunities.
• Listen for next product needs and coordinate with Account Executive when ready to close.
• Drive adoption and monitor fund utilization; identify accounts not using what they bought.
• Run customer workshops and webinars; share product updates to keep customers current.
• Route issues to Support/Product/AE while keeping HubSpot up to date in real time.
• Track metrics: customer meeting hours and product adoption; publish weekly and monthly NRU.

Skills

Customer Success

Account Management

SaaS

Communication

Tools

HubSpot

Job description

AwardSpring is seeking a Customer Success Manager in Chicago to own customer health from onboarding to renewal and upsell. You will be the single point of contact, resolving requests, routing to Support/Product/AE, and escalating early when risk appears.

You will drive renewals, upsell add-ons, and run workshops to increase product adoption, with a strong emphasis on proactive communication and CRM hygiene in HubSpot. This hybrid role is based in Chicago with a mature, AI-enabled product suite.