B2B Payments Sales Leader and Hunter at Finexio in Chicago, IL

About Finexio

Finexio is the leader in AP Payments as a Service, the leading embedded payments approach for business-to-business payments. We simplify the way businesses process and receive B2B payments by integrating electronic payments and cash flow improvement solutions directly into customers' accounts payable and procurement software.

We are growing rapidly, processing billions of dollars annually, and are a leading disruptor in the B2B Payments and Fintech industry. The company has raised over $75M in investment and is backed by investors including JP Morgan, Capital One, NBH Bank, Mendon Venture Partners, and Valley Bank.

The Role- Sales Hunter and Leader

This is not a maintenance role. We are seeking a hands-on Sales Leader to hunt, sell, and close CFOs who will personally carry a quota, close deals, and simultaneously build, refine, and enforce the sales processes and training programs that will scale our team. You will be held accountable to specific metrics, and you will hold your team to the same standard.

You will report directly to the CEO and will have high visibility and autonomy—but with that comes high accountability. We need someone who executes fast, documents everything, and drives results from day one.

What You Will Do

Carry a Personal Quota & Close Deals

• Personally close 10-13 mid-market corporate accounts ($50M-$200M+ in AP spend) annually

• Run your own pipeline: prospecting, discovery, demos, proposals, and closes

• Lead by example—your team will see you in the trenches daily

Build, Document, and Enforce Sales Processes

• Create and maintain sales playbooks, scripts, objection handling guides, and enablement materials

• Implement structured onboarding: new hires are productive within 30 days with clear milestones

• Ensure team members are set up on existing systems (dialers, call recording, CRM workflows) within their first week

• Run weekly roleplay sessions and call reviews—no exceptions

Drive Metrics Visibility & Accountability

• Deliver weekly metrics reports to leadership covering activity, conversion rates, and pipeline progression

• Hold weekly team meetings focused on: Metrics Review, Roleplay/Skills, and QA

• Ensure SDRs are booking 3-4 qualified meetings per week within 60 days of hire

• Track and report on: calls made, emails sent, conversations, meetings set, meetings held, opportunities created, proposals sent, and closes

• Identify underperformance early and address it directly—coaching or exiting within 90 days

Own CRM & Sales Operations

• Ensure 100% of sales activities are logged in Salesforce—pipeline hygiene is non-negotiable

• Leverage existing tools (Salesforce, ZoomInfo, call recording, email automation) before requesting new ones

• Build dashboards and reports that provide real-time visibility into team and individual performance

What Success Looks Like

First 30 Days:

• Complete onboarding with full product and process knowledge

• Audit existing team processes, tools, and pipeline

• Deliver first metrics report to CEO

• Begin personal prospecting and pipeline development

First 60 Days:

• Documented sales playbook and training materials in place

• Team fully utilizing existing systems with call recording reviews happening weekly

• Weekly metrics cadence established and consistently delivered

• Personal pipeline building toward quota

First 90 Days:

• SDRs hitting 3-4 qualified meetings per week

• First personal close or advanced-stage opportunity

• Clear performance trajectory for all team members with documented improvement plans where needed

Requirements

Non-Negotiables

• 5-10 years of B2B payments experience with verifiable quota attainment

• Track record of personally closing mid-market deals ($50M-$500M AP spend accounts)

• Experience building sales processes and training programs from scratch—not just inheriting them

• Demonstrated history of managing SDR/AE teams to specific, measurable outcomes

• Advanced Salesforce proficiency—you can build reports, dashboards, and workflows yourself

• Comfortable in a fast-paced environment where you execute first and refine later

Who You Are

• A doer, not a delegator—you prefer to build it yourself before handing it off

• Metrics-obsessed—you track everything and make decisions based on data

• Process-driven—you document what works and hold people accountable to following it

• Direct communicator—you address issues immediately, not after they fester

• High urgency—you move fast, follow up relentlessly, and don't let things slip

• Resourceful—you leverage existing tools and systems before asking for new ones

• Thick-skinned—you thrive on direct feedback and give it in return

Required Technical Skills

• Salesforce (advanced): pipeline management, reporting, dashboards, workflow automation

• Sales engagement tools: experience with dialers, call recording, email automation platforms

• ZoomInfo or similar prospecting tools

• Sales cycle management for 3-9 month complex B2B sales

• AI tools: you use AI daily for email drafting, research, training content, and productivity

Why Finexio

• Direct access to CEO with high visibility and autonomy

• Opportunity to build and own the sales function at a high-growth company

• Competitive base salary plus uncapped commission

• Equity/stock options

• Medical, dental, and vision

• Flexible PTO

This role is not for everyone. If you want to manage from a distance, wait for processes to be handed to you, or avoid personal accountability to a quota, this isn't the right fit. But if you're energized by building, closing, and leading by example—we want to talk to you.

Compensation - $125k - $150 Base Salary (Uncapped Commission - OTE $225k-$250k) + Equity

* If team targets are being met, there is potential for additional incentive.