Senior AE -> Sales Lead & Future Head of Sales

Bolto; San Francisco, Seattle, Chicago (CA, WA, IL); On-site; USD 180,000 - 300,000; Full time

Benefits offered by this job

Equity 0.15%-0.25%

OTE ~2x base

Job summary

Bolto is hiring a Senior AE who will grow into a future Head of Sales. You will own a personal pipeline, close opportunities, and help shape our sales playbook across SMB and mid-market segments.

The role collaborates closely with founders and executives to scale an AI-powered payroll/HR platform and build a high-impact team. You’ll join a small team in a fast-moving startup, with a compensation structure including equity and OTE.

Qualifications

• Proven B2B sales performance with clear quota attainment.
• Experience generating pipeline and owning the full sales cycle.
• Strong discovery, qualification, and negotiation skills.
• Evidence of coaching or leading other sellers.
• Experience improving sales processes and messaging.
• Willingness to take on leadership responsibilities in a startup.

Responsibilities

• Generate pipeline and carry a personal sales quota.
• Run discovery, demos, negotiations, and closing conversations.
• Help build a repeatable sales process across SMB and mid-market.
• Coach AEs and SDRs through calls and reviews.
• Assist in recruiting, onboarding, and developing new sellers.
• Partner with founders on territories, quotas, and compensation.
• Maintain accurate forecasts and identify risks early.
• Incorporate customer feedback into product and GTM decisions.

Skills

B2B sales

Quota attainment

Pipeline generation

Coaching

Leadership

Job description

Senior AE -> Sales Lead & Future Head of Sales

AI Powered All-In-One Payroll, HR + Recruiting

Location San Francisco, CA, US / Seattle, WA, US / Chicago, IL, US

We’re building next-gen Workday: one AI-native platform connecting recruiting, payroll, and HR so companies can hire, pay, and manage their teams in one place.

We’re backed by Standard Capital, General Catalyst, Y Combinator, and founders and executives from leading startups and Fortune 500 companies.

The opportunity

We’re hiring an exceptional seller who wants to help build and eventually lead our sales organization.

You’ll work directly with our cofounders/execs to close business, improve our sales approach, and develop the team. This role is a strong fit for a top-performing AE who has begun coaching others, building sales processes, or leading a small team—and is ready for greater ownership.

Our sales team currently includes two full-cycle sellers, supported by founders and executives. We’re also hiring AEs and SDRs across EOR and SMB sales. You’ll help shape how this growing team prospects, qualifies opportunities, wins customers, and measures performance.

You should enjoy creating your own pipeline and carrying a quota while helping other sellers succeed.

Your first 90 days

First 30 days: Learn the product and get into deals.
Work alongside the founders and current sellers, join customer conversations, and begin building your own pipeline. Learn why customers buy, where deals stall, and how we can improve discovery, messaging, and follow-up.

Days 31-60: Own opportunities and improve execution.
Manage your own deals from discovery through negotiation and close. Start building - test outbound approaches, strengthen qualification and pipeline discipline, and begin coaching teammates using what you’re learning.

Days 61-90: Build an approach the team can repeat.
Document effective messaging and sales practices, establish a useful pipeline review cadence, and help assess and onboard new hires. Work with the founders to define the next stage of your leadership responsibilities.

We’ll agree on ramp expectations and specific targets when you join, based on the segment and opportunities you own.

What you’ll own

• Generate pipeline and carry a personal sales quota.
• Run discovery, demos, negotiations, and closing conversations.
• Help build a repeatable sales process across SMB and mid-market customers.
• Coach AEs and SDRs through call reviews, deal strategy, and actionable feedback.
• Help recruit, assess, onboard, and develop new sellers.
• Partner with the founders on territories, quotas, compensation design, and performance expectations.
• Maintain accurate forecasts and identify risks early.
• Bring customer feedback into product and go-to-market decisions.

As you demonstrate sustained selling results and effective leadership, your responsibilities can expand into ownership of the sales organization. Progression toward Head of Sales will reflect your ability to build a team that performs consistently.

What you bring

• A record of strong B2B sales performance, supported by clear examples of quota attainment, peer ranking, and new business wins.
• Experience generating your own pipeline and managing the full sales cycle.
• Strong discovery, qualification, and negotiation skills.
• Evidence that you’ve helped other sellers improve through coaching, onboarding, or team leadership. Formal management experience is a must.
• Experience improving a sales process, message, or workflow and explaining the results.
• Comfort working at a startup where you help create the structure you need.
• A desire to remain close to customers and carry a quota while taking on leadership responsibilities.
• Have sold to the mid-market or enterprise layer before.

Experience selling payroll, HR software, fintech, or EOR services is helpful, but we welcome exceptional sellers from other B2B categories.

Why this role

You’ll join while the team is small enough for your decisions to have a visible impact. You’ll work directly with the founders, influence who we hire, and help establish how we sell.

Bolto connects several closely related customer needs: finding talent, paying employees, and managing HR. You’ll help determine how we turn those capabilities into a clear buying decision—and build the team that brings Bolto to more companies.

Location, compensation, and benefits

This is a full-time, in-person role based in San Francisco, Seattle, or Chicago.

• OTE: Approximately twice base salary, depending on the agreed compensation plan
• Equity: 0.15%-0.25%, with additional equity considered as responsibilities and impact grow.
• Fully covered medical, dental, and vision insurance.

At Bolto, we’re going after the traditional HR landscape by building an AI powered all-in-one platform where clients can seamlessly source, hire, manage, and pay their talent globally. We’re funded by top Silicon Valley investors including Y Combinator, Standard Capital, General Catalyst, Alumni Ventures, and more.

Our vision is ambitious: to become the world’s largest HR provider by delivering innovative solutions that simplify workforce management.

Join us in transforming how companies build and manage their teams!