Sr. Director, Head of Sales Enablement (Remote)
RevOps Report · Oak Brook, IL · 4 wk ago
Business Development$190k/yrFull-time
We need to output HTML fragment with sections: About the role (maybe from "About This Role"), Responsibilities (duties), Requirements (Education & Experience, Skills & Abilities, Other Requirements?), Benefits (if present), Pay (Compensation), Schedule (if present). Must not include headings with filler. Must not repeat job title. Must not include Job ID etc. Must remove boilerplate like EEO, legal, application instructions. Also remove navigation, cookie, etc. The posting includes many paragraphs; we need to preserve substantive info.
We need to decide sections: "About the role" (the initial paragraph about reporting, role description). Then "Responsibilities" (list of duties). Then "Requirements" (Education & Experience, Skills & Abilities, Other Requirements). Then "Benefits" (list of benefits). Then "Pay" (Compensation range). Then maybe "Schedule" if present: there is mention of remote status and role locations, requirement to work in-office minimum 4 days per month for employees within 90-min radius. That's schedule info. So we can include Schedule section.
We must not include sections with filler like "commensurate with experience". Not present.
We must use for section headings. Use
for section headings. Use - for any list of duties/requirements/benefits. Use
for prose.
We need to preserve all substantive info, not invent or summarize away detail. So we need to include details like "Owns onboarding and ramp for all new GTM hires - sellers, partnerships, and account management - with milestones, certification, and ramp targets that shorten time-to-productivity" etc. We'll need to convert each bullet into
- . The original duties are in paragraphs with headings like "Onboarding, Training & Field Readiness", "Content, Proposals & Competitive Intelligence", etc. We can treat each as a list item under Responsibilities.
Similarly for Requirements: Education & Experience (minimum required, additional preferred). Skills & Abilities (list). Other Requirements (travel, lifting, sitting). We'll need to preserve those.
Benefits: list includes healthcare, 401K savings plan, company holidays, paid time off, parental leave, employee assistance program. Also maybe "industry-leading benefits including, but not limited to:" So we list those.
Pay: Compensation: $190,000-$220,000 per year.
Schedule: remote status and role locations subject to change, relocation not provided. Employees within 90-minute radius of Oak Brook, IL headquarters required to work in-office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.
We need to ensure we don't include boilerplate like "Other duties as assigned." That's substantive? It's a generic phrase but maybe we keep it as part of responsibilities? It's not specific detail; but it's part of posting. The instruction: preserve ALL substantive information; do NOT invent or summarize away detail. "Other duties as assigned." is a generic line but it's in the posting; we could keep it as a list item? It's not a specific duty but it's still part of the posting. Might be considered filler? It's not a placeholder like "N/A". I'd keep it.
Also need to remove "Take the next step..." etc which is application instructions and boilerplate. Also remove "Learn more at inspirafinancial.com." etc. Also remove "Our values shape..." etc. Also remove "Don't meet every single requirement?" etc. Also remove "Remote status and role locations are subject to change, and relocation is not provided.*Employees within a 90‑minute radius..." Actually that part is schedule info; we keep that but need to remove the asterisk and footnote? The footnote about support specialist positions. We'll keep the sentence.
We need to output only HTML fragment, no markdown fences.
Let's craft.
Structure:
About the role
...
Responsibilities
- Onboarding, Training & Field Readiness: Owns onboarding and ramp for all new GTM hires - sellers, partnerships, and account management - with milestones, certification, and ramp targets that shorten time-to-productivity. Runs a year-round learning curriculum across product, platform, and segment-specific selling (SMB, Mid-Market, and Enterprise), and readies the field for the First Dollar platform migration. Establishes demo and product certification, and equips frontline managers with coaching frameworks, call-review, and deal-inspection tools.
- Content, Proposals & Competitive Intelligence: Builds and governs the sales content system - pitch decks, one-pagers, battle cards, ROI tools, and templates - and the knowledge management systems that put the right information in front of sellers at the right moment. Develops and maintains sales playbooks that align process and messaging across the buyer journey. Translates Marketing's positioning and messaging into field-ready tools - talk tracks, pitch certification, and objection handling - and verifies the message shows up in live selling. Partners with Product and Technology to reflect product and platform updates in internal and external collateral. Leads the RFP and proposal function, maintaining a scalable response knowledge base and partnering with Sales and Marketing to strengthen GTM materials and improve win rate. Arms the field with competitive intelligence to position Inspira against alternatives. Collaborates with Marketing to ensure alignment between marketing campaigns and broader H&B GTM strategy, maximizing lead conversion and client engagement.
- Partner & Channel Enablement: Equips brokers, consultants, and National Accounts partners with the tools, training, and second-sell capability to prioritize and sell Inspira's suite. Partners with Sales and Marketing on broker enablement and incentive programs that make Inspira the easiest suite for partners to sell.
- AI & Sales Productivity: Owns the rollout and adoption of AI tools (including Claude) across the GTM organization - prompt libraries, AI-assisted workflows, and certification - for account research, call prep, proposal generation, and follow-up. Tracks and grows the ROI of AI in sales (hours saved, proposal velocity, win-rate lift, cost-to-serve), and keeps AI use within Inspira's data and governance standards.
- Systems, Reporting & Metrics: Owns sales analytics and performance reporting that support leadership decision-making and day-to-day sales management. Drives consistent, effective use of CRM across the sales organization in partnership with Technology. Runs the enablement operating rhythm - intake, prioritization, launch calendar, and feedback loops - and leads change management for GTM initiatives. Supports the evolution of H&B go-to-market strategy, helping define and prioritize the initiatives that maximize Inspira's rate of growth.
- Other duties as assigned.
Requirements
We could split into sub-sections? But instruction: use for section headings. Could have multiple sections: Education & Experience, Skills & Abilities, Other Requirements. But they said prefer a few substantive sections over many thin ones. However we need to preserve all info. Could combine Education & Experience and Skills & Abilities under one Requirements section with lists. But we need to use - for any list of duties/requirements/benefits. So we can have a
for requirements items. However we have multiple categories; we could still list each as - with the category text. That might be okay.
But we need to preserve details like "Minimum Required 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required". That's a sentence. We'll put as
- .
"Additional Preferred Experience in health and benefits, insurance, or financial services go-to-market preferred Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred Applied experience deploying AI or LLM-based tools to a sales organization preferred". That's a bit messy; we need to preserve exactly. We'll keep as a sentence.
Skills & Abilities list: many bullet-like sentences separated by line breaks. We'll convert each to
- .
Other Requirements: "Infrequent travel (20%)Ability to provide personal transportation from time to timeOccasionally lifts up to 25 poundsProlonged periods of sitting at a desk and working on a computer". We'll keep as
- maybe combine.
We'll output:
Requirements
- Minimum Required: 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams. Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required.
- Additional Preferred: Experience in health and benefits, insurance, or financial services go-to-market preferred. Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred. Applied experience deploying AI or LLM-based tools to a sales organization preferred.
- Skills & Abilities: A builder who has stood up or scaled a function, and a player-coach comfortable both leading and doing. A talent magnet who can recruit, develop, and inspire a growing team. Proven track record building onboarding, training, playbooks, and content that measurably improved sales performance. Expertise in optimization and deployment of sales technologies, such as: CRM (Salesforce/HubSpot), engagement (Outreach/Gong/SalesLoft), RFP support (Loopio), lead qualification (ZoomInfo, LinkedIn Sales Navigator). Deep understanding of the health and benefits sales process, including broker/consultant and National Accounts distribution. Ability to translate product, positioning, and competitive insight into clear, field-ready messaging. Strong content strategy and governance instincts, with comfort using Salesforce and BI/analytics tools. Highly organized, with the ability to run multiple initiatives simultaneously without losing the thread. Strong executive presence and communication skills; comfortable operating with ambiguity and building in a still-forming organization.
- Other Requirements: Infrequent travel (20%). Ability to provide personal transportation from time to time. Occasionally lifts up to 25 pounds. Prolonged periods of sitting at a desk and working on a computer.
Benefits:
Benefits
- Healthcare
- 401K savings plan
- Company holidays
- Paid time off
- Parental leave
- Employee assistance program
Pay:
Pay
Compensation: $190,000‑$220,000 per year
Schedule:
Schedule
Remote status and role locations are subject to change, and relocation is not provided. Employees within a 90‑minute radius of our Oak Brook, IL headquarters are required to work in‑office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.
We must ensure we didn't include any boilerplate like "Take the next step..." etc. We excluded.
Check for any repeated lines: we didn't include "Other duties as assigned." we included as a list item under Responsibilities.
Check for any placeholder like "commensurate with experience" - not present.
Check for any "N/A" etc - none.
Check for any "varies" - we have compensation range, not varies.
Check for any "TBD" - none.
Now output only HTML fragment.
Make sure to escape any special characters? The text includes ampersand (&) in "H&B". Should we keep as is? In HTML, & is entity start; we need to escape as &. The instruction says output HTML fragment
for prose. We need to preserve all substantive info, not invent or summarize away detail. So we need to include details like "Owns onboarding and ramp for all new GTM hires - sellers, partnerships, and account management - with milestones, certification, and ramp targets that shorten time-to-productivity" etc. We'll need to convert each bullet into
About the role
...
Responsibilities
- Onboarding, Training & Field Readiness: Owns onboarding and ramp for all new GTM hires - sellers, partnerships, and account management - with milestones, certification, and ramp targets that shorten time-to-productivity. Runs a year-round learning curriculum across product, platform, and segment-specific selling (SMB, Mid-Market, and Enterprise), and readies the field for the First Dollar platform migration. Establishes demo and product certification, and equips frontline managers with coaching frameworks, call-review, and deal-inspection tools.
- Content, Proposals & Competitive Intelligence: Builds and governs the sales content system - pitch decks, one-pagers, battle cards, ROI tools, and templates - and the knowledge management systems that put the right information in front of sellers at the right moment. Develops and maintains sales playbooks that align process and messaging across the buyer journey. Translates Marketing's positioning and messaging into field-ready tools - talk tracks, pitch certification, and objection handling - and verifies the message shows up in live selling. Partners with Product and Technology to reflect product and platform updates in internal and external collateral. Leads the RFP and proposal function, maintaining a scalable response knowledge base and partnering with Sales and Marketing to strengthen GTM materials and improve win rate. Arms the field with competitive intelligence to position Inspira against alternatives. Collaborates with Marketing to ensure alignment between marketing campaigns and broader H&B GTM strategy, maximizing lead conversion and client engagement.
- Partner & Channel Enablement: Equips brokers, consultants, and National Accounts partners with the tools, training, and second-sell capability to prioritize and sell Inspira's suite. Partners with Sales and Marketing on broker enablement and incentive programs that make Inspira the easiest suite for partners to sell.
- AI & Sales Productivity: Owns the rollout and adoption of AI tools (including Claude) across the GTM organization - prompt libraries, AI-assisted workflows, and certification - for account research, call prep, proposal generation, and follow-up. Tracks and grows the ROI of AI in sales (hours saved, proposal velocity, win-rate lift, cost-to-serve), and keeps AI use within Inspira's data and governance standards.
- Systems, Reporting & Metrics: Owns sales analytics and performance reporting that support leadership decision-making and day-to-day sales management. Drives consistent, effective use of CRM across the sales organization in partnership with Technology. Runs the enablement operating rhythm - intake, prioritization, launch calendar, and feedback loops - and leads change management for GTM initiatives. Supports the evolution of H&B go-to-market strategy, helping define and prioritize the initiatives that maximize Inspira's rate of growth.
- Other duties as assigned.
Requirements
We could split into sub-sections? But instruction: use for section headings. Could have multiple sections: Education & Experience, Skills & Abilities, Other Requirements. But they said prefer a few substantive sections over many thin ones. However we need to preserve all info. Could combine Education & Experience and Skills & Abilities under one Requirements section with lists. But we need to use - for any list of duties/requirements/benefits. So we can have a
for requirements items. However we have multiple categories; we could still list each as - with the category text. That might be okay.
But we need to preserve details like "Minimum Required 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required". That's a sentence. We'll put as
- .
"Additional Preferred Experience in health and benefits, insurance, or financial services go-to-market preferred Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred Applied experience deploying AI or LLM-based tools to a sales organization preferred". That's a bit messy; we need to preserve exactly. We'll keep as a sentence.
Skills & Abilities list: many bullet-like sentences separated by line breaks. We'll convert each to
- .
Other Requirements: "Infrequent travel (20%)Ability to provide personal transportation from time to timeOccasionally lifts up to 25 poundsProlonged periods of sitting at a desk and working on a computer". We'll keep as
- maybe combine.
We'll output:
Requirements
- Minimum Required: 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams. Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required.
- Additional Preferred: Experience in health and benefits, insurance, or financial services go-to-market preferred. Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred. Applied experience deploying AI or LLM-based tools to a sales organization preferred.
- Skills & Abilities: A builder who has stood up or scaled a function, and a player-coach comfortable both leading and doing. A talent magnet who can recruit, develop, and inspire a growing team. Proven track record building onboarding, training, playbooks, and content that measurably improved sales performance. Expertise in optimization and deployment of sales technologies, such as: CRM (Salesforce/HubSpot), engagement (Outreach/Gong/SalesLoft), RFP support (Loopio), lead qualification (ZoomInfo, LinkedIn Sales Navigator). Deep understanding of the health and benefits sales process, including broker/consultant and National Accounts distribution. Ability to translate product, positioning, and competitive insight into clear, field-ready messaging. Strong content strategy and governance instincts, with comfort using Salesforce and BI/analytics tools. Highly organized, with the ability to run multiple initiatives simultaneously without losing the thread. Strong executive presence and communication skills; comfortable operating with ambiguity and building in a still-forming organization.
- Other Requirements: Infrequent travel (20%). Ability to provide personal transportation from time to time. Occasionally lifts up to 25 pounds. Prolonged periods of sitting at a desk and working on a computer.
Benefits:
Benefits
- Healthcare
- 401K savings plan
- Company holidays
- Paid time off
- Parental leave
- Employee assistance program
Pay:
Pay
Compensation: $190,000‑$220,000 per year
Schedule:
Schedule
Remote status and role locations are subject to change, and relocation is not provided. Employees within a 90‑minute radius of our Oak Brook, IL headquarters are required to work in‑office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.
We must ensure we didn't include any boilerplate like "Take the next step..." etc. We excluded.
Check for any repeated lines: we didn't include "Other duties as assigned." we included as a list item under Responsibilities.
Check for any placeholder like "commensurate with experience" - not present.
Check for any "N/A" etc - none.
Check for any "varies" - we have compensation range, not varies.
Check for any "TBD" - none.
Now output only HTML fragment.
Make sure to escape any special characters? The text includes ampersand (&) in "H&B". Should we keep as is? In HTML, & is entity start; we need to escape as &. The instruction says output HTML fragment
- for any list of duties/requirements/benefits. So we can have a
- for requirements items. However we have multiple categories; we could still list each as
- with the category text. That might be okay. But we need to preserve details like "Minimum Required 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required". That's a sentence. We'll put as
- . "Additional Preferred Experience in health and benefits, insurance, or financial services go-to-market preferred Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred Applied experience deploying AI or LLM-based tools to a sales organization preferred". That's a bit messy; we need to preserve exactly. We'll keep as a sentence. Skills & Abilities list: many bullet-like sentences separated by line breaks. We'll convert each to
- . Other Requirements: "Infrequent travel (20%)Ability to provide personal transportation from time to timeOccasionally lifts up to 25 poundsProlonged periods of sitting at a desk and working on a computer". We'll keep as
- maybe combine.
We'll output:
Requirements
- Minimum Required: 12+ years of experience in sales enablement, sales operations, or go-to-market, including 4+ years leading teams. Bachelor's degree in Business, Marketing, Healthcare, or a related field, or an equivalent combination of education, experience, and training, required.
- Additional Preferred: Experience in health and benefits, insurance, or financial services go-to-market preferred. Experience enabling channel partners - brokers, consultants, or distributors - to sell preferred. Applied experience deploying AI or LLM-based tools to a sales organization preferred.
- Skills & Abilities: A builder who has stood up or scaled a function, and a player-coach comfortable both leading and doing. A talent magnet who can recruit, develop, and inspire a growing team. Proven track record building onboarding, training, playbooks, and content that measurably improved sales performance. Expertise in optimization and deployment of sales technologies, such as: CRM (Salesforce/HubSpot), engagement (Outreach/Gong/SalesLoft), RFP support (Loopio), lead qualification (ZoomInfo, LinkedIn Sales Navigator). Deep understanding of the health and benefits sales process, including broker/consultant and National Accounts distribution. Ability to translate product, positioning, and competitive insight into clear, field-ready messaging. Strong content strategy and governance instincts, with comfort using Salesforce and BI/analytics tools. Highly organized, with the ability to run multiple initiatives simultaneously without losing the thread. Strong executive presence and communication skills; comfortable operating with ambiguity and building in a still-forming organization.
- Other Requirements: Infrequent travel (20%). Ability to provide personal transportation from time to time. Occasionally lifts up to 25 pounds. Prolonged periods of sitting at a desk and working on a computer.
Benefits
- Healthcare
- 401K savings plan
- Company holidays
- Paid time off
- Parental leave
- Employee assistance program
Pay
Compensation: $190,000‑$220,000 per year
Schedule:Schedule
Remote status and role locations are subject to change, and relocation is not provided. Employees within a 90‑minute radius of our Oak Brook, IL headquarters are required to work in‑office a minimum of 4 days per month from 10 am to 2 pm, with at least one day falling on a Monday or Friday. This requirement does not apply to support specialist positions.
We must ensure we didn't include any boilerplate like "Take the next step..." etc. We excluded. Check for any repeated lines: we didn't include "Other duties as assigned." we included as a list item under Responsibilities. Check for any placeholder like "commensurate with experience" - not present. Check for any "N/A" etc - none. Check for any "varies" - we have compensation range, not varies. Check for any "TBD" - none. Now output only HTML fragment. Make sure to escape any special characters? The text includes ampersand (&) in "H&B". Should we keep as is? In HTML, & is entity start; we need to escape as &. The instruction says output HTML fragment