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Pre & Post Go-To-Market Portfolio
Pre/post GTM and Tech "Pinch Hitter"
I'm a flexible, impact-driven team player who thrives in fast-paced, high-growth environments. While my core expertise is in technical recruiting, I’ve successfully stepped in to source and hire for both pre and post Go-To-Market (GTM) roles when needed. This adaptability has allowed me to support cross-functional teams and deliver results wherever the business has required coverage.
GTM Experience by Company
SHOPIFY (Q4/2024 – Maternity Cover)
Roles Supported: Enterprise Solutions Engineers and Account Executives
Responsible for sourcing high-caliber talent to drive Shopify’s expansion into retail enterprise markets, closely evaluating candidates through comprehensive 'Life Story' interviews aligned with our PLG culture.
BABYLON HEALTH (2021–2022)
Roles Supported: Account Execs, Sales Reps, Customer Service
In addition to Software Engineering I was tasked to help rapidly build Babylon’s first U.S. GTM team prior to IPO. The bar was high and very niche. I targeted talent comfortable with ambiguity and rapid change in regulated healthcare environments.
INTAKE EXAMPLE: Shopify Retail Enterprise Account Executive roles
I had inherited this role from from a teammate who had gone on maternity and I had several questions. This was my first discussion with the Head of Shopify’s Retail AE org.
Me: The previous Sourcer passed on your requirements.. they’re a little confusing and I’d like to really focus on why those traits are so important.
HM: OK, basically we need someone adept with ambiguity, experienced in large enterprise sales cycles, and skilled at collaborative selling with Solutions Engineers.
Me: Could we get more specific about their sales backgrounds—should they primarily come from software, hardware or both? And why is hardware important?
HM: Shopify’s usual eCommerce product is either out of the box SaaS or, if custom, a headless API that POS systems easily integrate with. No hardware required for that.
But, our Enterprise Retail Point of Sale (POS) solutions offer both software and hardware (physical in-store POS systems). That’s why the candidates I’m looking for need experience in both retail specific software and hardware.
Me: So the plan is to sell into enterprise clients (Sephora, REI, etc.) that have legacy POS and replace it with Shopify’s modern POS software/hardware, correct?
HM: Yes
Me: OK does this person need to be familiar with both older/legacy POS software and hardware solutions as well as modern ones?
HM: That’s ideal, candidates who have moved from being AEs for companies like NCR, Netsuite, Toshiba, etc. into modern Enterprise POS solutions like Salesforce/Oracle/Square..that would be best
Me: Got it, what if they have the legacy piece but only have modern POS systems built for SMB to midmarket like Toast, Clover or Lightspeed?
HM: Maybe, if their stellar, but Enterprise AEs sales-cycle can take from 1-2 years per client. That takes a different kind of approach and mentality than SMB/Mid-Market.
Me Besides legacy/modern Enterprise Software / Hardware what are you most critical requirements?
HM: Ability to thrive in an ambiguous landscape, excels at high-level (c-suite) relationship build and consultative selling, understanding complex business cases (every major retailer has different needs for their POS), customization of enterprise technology solutions, the ability to talk shop about the client’s current environment.
Me: Why is it so important for them to be able to ‘talk shop’ about the client’s current environment?
HM: The AE needs to be able to tap into what the customer’s journey at retailer ‘x’ looks like—from entering the door to payment—so our headless POS software and physical hardware can be tailored effectively to each business’ specific needs.
Me: Who are we explicitly NOT targeting?
HM: Transactional sellers lacking strategic selling skills or who are uncomfortable in ambiguous environments.
Me: Target market segment?
HM: Enterprise retailers between $40M–$250M ARR, including private equity-owned brands.
Me: Preferred talent sources?
HM: Enterprise AEs from..
Q: Compensation structure?
A: Base: $150K–$180K, 50% OTE, equity component, accelerators available.
Me: Can we push this if, for instance, a candidate is from Salesforce?
HM: Case by case basis but, generally, if they are stellar, we have some room to make the numbers work
Accomplishments
This HM was short on time but, by pushing for clarity during the intake, I was able to move beyond vague requirements and uncover the specific skills, experiences, and business context that truly defined success in the role. I clarified must-haves like enterprise POS experience across both software and hardware, and gained a clear picture of the ideal candidate’s career path—from legacy systems to modern enterprise solutions. I aligned with the hiring manager on key disqualifiers, surfaced the “why” behind each requirement, and walked away with prioritized sourcing targets and clear compensation parameters. Most importantly, I gained a deeper understanding of how this role contributes to Shopify’s broader strategy, which allows me to engage candidates with purpose, precision, and confidence.
INTERVIEW EXAMPLE: Summarized Life Story Interview with Sophia (fictional) an Enterprise Account Executive at Salesforce
Kicked off our conversation by sharing Shopify’s recent expansion into the enterprise retail space, highlighting our new Enterprise POS solution. I explained how our product-led growth approach differs from traditional enterprise sales, touching on our fast-moving culture and clear opportunities for rapid upward mobility due to fact that this org was brand-new within Shopify.
Sophia then shared details about her role at Salesforce, specifically her experience managing complex sales cycles within the financial services sector. She highlighted her ability to navigate senior-level stakeholders, optimize territories strategically, and coordinate cross-functionally.
Then I transitioned into the ‘Life Story’ portion of the interview, framing it as a conversation designed to dive deep into three key areas that are essential for success at Shopify:
Growth Mindset
I started with, “Sophia, you mentioned you made the jump from Workday to Salesforce to stretch yourself. What drove you to seek that growth, specifically in terms of your skills?” Sophia explained she felt she'd hit a growth ceiling at Workday and intentionally sought the complexity Salesforce offered.
I probed further, “When you joined Salesforce, were there gaps or unexpected challenges you ran into, and how did you tackle those?” She openly discussed facing a learning curve on highly regulated financial deals. Sophia shared she proactively leaned into mentorship from senior team members, took ownership of her professional development, and quickly mastered new domain knowledge.
To make sure I understood her learning style, I asked, “Could you tell me about one particular deal where your mindset of constant learning made the difference?” Sophia recounted a scenario in which she successfully navigated complex regulatory objections, demonstrating how her proactive learning directly impacted a multimillion-dollar deal.
Over-sized Impact
Next, I steered the conversation towards her ability to drive meaningful results: “You mentioned earlier you exceeded your quota by 150%—that’s impressive. Walk me through your exact role in making that happen.” Sophia clearly explained her leadership in orchestrating cross-functional teams, aligning internal stakeholders, and ensuring strategic engagement with the customer’s executive suite.
I pressed gently but firmly, “What specific hurdles did you run into internally or externally, and how exactly did you clear them?” Sophia shared openly about navigating internal resource constraints and conflicting priorities, describing specifically how she gained alignment from senior Salesforce leadership by clearly communicating the strategic importance of the account.
To further assess her self-awareness, I asked, “Reflecting back, is there something you might have done differently to make that outcome even better?” She thoughtfully mentioned earlier identification of certain customer objections could have accelerated the deal even further, reflecting genuine introspection and awareness.
High Rung Thinking
To gauge strategic perspective, I asked, “From your vantage point at Salesforce, what trends do you see reshaping the enterprise retail landscape today?” Sophia comfortably discussed the shift towards headless commerce, omni-channel expectations, and the increasing demand for deeply customizable solutions.
Continuing, I asked, “If you joined Shopify tomorrow, how would you position our enterprise POS solutions against established competitors like NCR or Oracle?” Sophia had done her homework and confidently outlined Shopify’s differentiation around speed to market, ease of customization, and how our headless POS + hardware could uniquely meet enterprise retailers’ evolving needs.
To test her strategic foresight, I challenged, “From your viewpoint, what’s the biggest hurdle Shopify faces in gaining traction with larger enterprise retailers?” Sophia said inertia and vendor lock-in with enterprise customers are the biggest challenge. I asked “How have you overcame that at Salesforce”? She immediately described proactive approaches like targeted proof-of-concept programs (partnering with SFDC Solutions Engineering) and tailored c-suite messaging that clearly highlights the agility and risk reduction inherent to the solution.
Comp and Career Growth discussion
I presented Sophia with Shopify’s unique Enterprise Account Executive compensation (their "Total Wallet" philosophy). Total wallet encompassing base, equity (RSUs), and incentive compensation. At hire total wallet typically ranges from $150K–$275K, and is based on experience + interview performance.
A $200K total wallet, for instance, would look like:
Result
Although Sophia’s current total compensation at Salesforce ($360K) exceeded Shopify’s projected $320K (for ‘normal’ performers), I focused on highlighting Shopify’s strong career mobility, the opportunity to make a tangible impact on the company’s bottom line and our uncapped incentives and accelerator gates. The growth trajectory for good to top performers was tangible—I emphasized that this was a new team within a new product area (essentially a startup within a startup) where she would play a foundational role in building processes from the ground up. Happily, Sophia accepted an offer shortly after my contract ended.
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