Head of Sales (Closer)

Single Grain; Oregon; Hybrid; USD 150,000 - 200,000; Full time

Benefits offered by this job

Healthcare

Dental & Vision

401(k) match

Unlimited PTO

Monthly UberEats

MacBook

Home-office stipend

Job summary

Single Grain, LLC is seeking a senior individual contributor to own the entire new-business cycle. You will source and close consultative marketing engagements at roughly $15k-$25k+ per month, with an annual target of multi-million dollars in new business and expansion opportunities.

You’ll lead discovery, proposals, pricing, and negotiations, then grow accounts with upsell and cross-sell while pursuing RFPs.

Qualifications

• 6+ years of B2B closing with personal quota.
• Experience owning a full sales cycle from discovery to close.
• Ability to grow accounts through upsell and cross-sell.
• Proven success in consultative marketing engagements at $15k-$25k+/month.
• Experience finding, responding to, and winning RFPs.

Responsibilities

• Own new-business number from first call to signature.
• Run discovery, write proposals, negotiate, and close deals.
• Grow accounts post-close via upsell and cross-sell across services.
• Find relevant RFPs, qualify and win them, with AI-assisted workflow.
• Maintain a clean CRM pipeline and weekly forecast.

Job description

Type: Full-time, senior individual contributor carrying the company's biggest new-business number. No team to manage. Deals: consultative marketing engagements at $15k-$25k+/month, sold to marketing and growth leaders Location: Full-time, remote (United States only; Los Angeles a huge plus) Comp: $150,000-$200,000 USD base plus variable; OTE around $400,000+

One-liner

Personally close consultative $15k-$25k+/month marketing engagements, then grow them, so new business no longer depends on the founder.

About the role

Single Grain combines marketing services, software, and AI. Eric Siu hosts Leveling Up and co-hosts Marketing School with Neil Patel, which gives us brand reach and deal flow most agencies do not have. This seat is the head salesperson: you run discovery, write the proposal, negotiate, and close. Then you grow the account with upsell and cross-sell, and you hunt RFPs and win a share. You should be an advanced AI user in your sales motion. Before every discovery call you have an AI-built brief on the company, its current marketing, and its likely buying committee. Your workflow first-drafts proposals and RFP responses, and you finish them. Follow-ups are drafted from your call notes the same day. AI does the prep so your hours go to the conversations that close; you still write the parts that win the deal.

What you will own

• Your own new-business number: qualified deals from first call to signature.
• Discovery, proposals, pricing within our rate card, and negotiation.
• Expansion of the accounts you close: upsell and cross-sell into more services.
• An RFP motion: find relevant RFPs, qualify them, and win them, with an AI scan that surfaces fits weekly against our criteria.
• An AI account-research + proposal workflow (call-prep brief, proposal and RFP first draft, follow-up from call notes) that a teammate also uses.
• A clean CRM pipeline and a weekly forecast you stand behind.

What success looks like

• By day 30: pipeline audited and owned in the CRM; offers learned; first proposals out; your AI research + proposal workflow is in use by a teammate on a live deal.
• By day 60: your own discovery-to-proposal cycle running on inbound and self-sourced deals; the weekly AI RFP scan is live; weekly forecast.
• By day 90: your first $15k+/month engagement closed personally; forecast within ±15%; Eric no longer needed in standard late-stage deals. Failure = pipeline still waiting on Eric to close.
• By 6-12 months: on pace for about $3M+ a year in closed new business, with expansion revenue and RFP wins on top.

Evidence we want to see

• 6+ years of B2B closing (ideally more), carrying a personal new-business quota. Director, VP, or Head titles are fine if you still carry your own number.
• About $3M+ a year personally closed, with the timeframe.
• Consultative agency, professional-services, or martech deals at roughly $15k-$25k+/month (about $180k+ ACV) sold to marketing or growth leaders.
• A concrete example of growing an account after the first deal.
• RFPs you found, answered, and won (strong plus).
• AI in your sales workflow you can show: a named workflow, what it does, the time it saves, and the parts you still write yourself.
• Steady tenure; internal promotions are a big plus.

What this role is not

• Not a sales manager role or team build. Not SDR/BDR, renewals-only, or customer success. Not SMB, transactional, or B2C selling. Not fractional or consulting. Not for anyone based outside the US.

How the process works

Application → 7 short questions sent to you by email → evidence review (redacted quota letters or CRM reports welcome) → live mock discovery call → paid, time-boxed practical on two sample accounts (a new-logo proposal and an expansion plan) with a live defense → references from former managers.

Benefits

• Medical, dental, and vision; life insurance; 401(k) with 4% match; unlimited PTO; monthly UberEats; MacBook; home-office stipend/setup. Subject to plan terms and eligibility.