TCT Exclusive: Dakota McKenzie, GTM @ Unusual Ventures

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We’re thrilled to announce this week’s exclusive with Dakota McKenzie, Senior Associate, GTM @ Unusual Ventures! Prior to joining Unusual Ventures, Dakota worked on the top performing Enterprise team at Segment, and was also an early sales hire at Databricks. Dakota’s operating experience helped catapult him onto the venture scene, where he now focuses on helping founders scale their sales and customer acquisition efforts. With deep domain expertise in all things GTM, we sat down and discussed:

  • The transition from Enterprise Sales → Venture Capital 🔁

  • How Unusual’s Get Ahead Platform accelerates Sales, Marketing & Recruiting 🧙🏼‍♂️

  • The 4 key elements that matter most at the Investor & Board level 🔢

  • How ICP’s help accelerate Product Market Fit 🤝

  • The ideal Enterprise tech stack 🖲

  • The future of Sales in 2025 🔮

TCT: Thanks for sitting down with us, Dakota. Let’s jump in.

How did you start out with regards to your career?

I learned what a premier SaaS company was like during my first internship in SaaS at Demandware (IPO, then acquired by $CRM). It was an incredible opportunity to learn the fundamentals of a high growth startup and experience a transition from late-stage growth to IPO. I noticed a change from a “win deals at all costs” approach to focusing on operational margins, growth metrics, building specific roles for the entire pre-sales and post-sales motions, and other critical IPO-readiness requirements. 

I eventually made my way out to the Bay Area to join Sumo Logic,  where I learned  how to drive complex technical deals and had the opportunity to work on a world-class Go-to-Market team. 

I was presented with the opportunity to join Databricks in the early days of the company and I felt this was a “can’t miss” career move due to the hype around Machine Learning, AI, and Spark. During my 2.5 year tenure, I built a greenfield territory from scratch, and made a strong contribution to the team while we grew from $10M - $100M ARR. This was one of the best experiences in my early career. Not only did I learn about one of the world’s most popular open-source projects at the early stages, but I consider this where I got my “Sales MBA.” I feel incredibly lucky to have been a part of the team at such an integral time and feel fortunate to have relationships with leaders at the organization. 

The opportunity presented itself to “build” again when I joined Segment as one of the first 10 Enterprise AE’s (Account Executive) as they expanded up-market to sell to Fortune 500s and revolutionize their customer data strategy. During my time, I exceeded my number alongside the top performing Enterprise team at the company. It was a tough decision to leave (as you may have heard they were recently acquired by Twilio, which says a lot about Segment’s opportunity in the market!), but I was presented with the opportunity to join Unusual Ventures and could not pass up the chance to work with multiple early stage companies at one time. I’m excited to share what’s so unique about Unusual and why I found this to be the next “can’t miss” opportunity in my career. 

You transitioned from enterprise sales to working at a Venture firm. What’s been the biggest learning curve to date?

Unusual’s Get Ahead Platform (GAP) team and the Unusual Method sold me on joining the firm and I’m excited to share with you why Unusual’s approach is so unique.

Starting a company is extremely difficult for a long list of reasons, but founders also get large sums of capital to start a company with the expectation that they know how to recruit, market, sell, and build a world-class product without much support. Unusual recognizes this thought process is backwards and through the Get Ahead Platform,  we’ve hired the best operators in Sales, Marketing, and Recruiting from world class companies — including MongoDB, Okta, AppDynamics, LaunchDarkly, and many others — to work inside portfolio companies for 3-6 months at a time helping founders execute on specific KPIs/OKRs to accelerate and improve their likelihood of raising a Series A investment. 

To clarify, the GAP Team does not just advise and conduct occasional check-ins. We take what we’ve learned from our experiences of building and scaling renowned companies and distill it down to  help early stage companies go from Idea to Product Market Fit. A lot of other firms have operating teams that say they work with founders, but in the form of the infrequent whiteboard session or introduction to someone outside the firm versus Unusual’s hands-on approach. The main difference in how Unusual works with founders, compared to other firms out there that also have a Platform team, is the GAP team members have the same OKRs as the portfolio company so its a joint fail/succeed model. If they don’t hit their milestones, neither do we.

Through our GAP engagements, we become an extension of our portfolio companies’ teams and our founders can measure our impact with the same metrics they would use with a full-time VP of Sales. Our engagements meet our founders where they are in their journey — from ideation around an ICP or product hypothesis all the way to closing deals and hitting a quarterly quota.

One major challenge has been trying to “codify” my learnings and playbooks I’ve built at other organizations and make it applicable to founders at the early stage. Our Field Guides are a perfect example of how we use our experience to accelerate the success of our portfolio companies. We’re building a lot of resources internally and with founders to improve this process each quarter. 

It’s one of the most exciting and rewarding jobs I’ve had to date and I’m thrilled to be a part of such a talented group. I haven’t even mentioned the caliber of our investment team (John Vrionis [Managing Partner], Andy Johns [former President of Wealthfront, helped build and grow social powerhouses like Facebook, Twitter, and Quora], Sarah Leary [co-Founder of Nextdoor], Noah Carr [Armorblox investor] , Rachel Star, and Jordan Segall) who I’ve had the pleasure of learning from consistently about investing and building renowned enterprise and consumer  companies. 

You’re currently a Senior Associate at Unusual Ventures. Tell us about your experience so far. What has been the most challenging aspect of the job? What’s been the most rewarding moment to date?

I have even greater admiration for early stage founders given the obstacles they have to overcome. My experience and expertise in certain areas on Go-to-Market certainly helps, but the challenge is finding the right sales motion depending on the market, team’s experience, and the adoption behaviors of ideal users and buyers. 

Matt Wells, the founder and CTO of Shujinko, shared an example that we see many founders experience

“As someone who managed a $25 million software budget in a previous life, I thought, “I bought enterprise software products before — this can’t be hard.” Wrong. Landing discovery meetings wasn’t an issue — given our domain expertise and backgrounds, my cofounder Scott and I were able to land initial discovery meetings with CIOs, CTOs, and CISOs at companies we were targeting. However, once we found ourselves running the initial meetings, handling the follow up, and trying to convert prospects into paying customers, we realized we were in uncharted territory.”

To simplify this challenge, our Get Ahead Platform team takes an approach similar to what an Engineer would do while building a product: Hypothesize, test, iterate, deploy, scale, etc. Our team works with founders day-to-day to build a disciplined and flexible process to not only execute in the early stages of their startup journey, but to impart the right frameworks to hire their first VP of Sales, VP of Marketing, Lead Recruiter, etc. 

From the beginning of our sales engagements, we try to get very specific about who to target and kick-off initial outreach. Recently, I worked with a portfolio company to kick off their first prospective customer conversations with the goal of 24 meetings in a quarter. In three months, they’ve met with over 60 different prospective customers and had a 4x response rate on outreach. 

Following on that example, after experiencing similar results with another startup, we were able to generate >$600K in pipeline in a quarter and are making strong progress to selling into Fortune 500 companies using a disciplined and structured sales process you’d typically see at the later stages of a company. 

Overall, as a team we’ve generated over $5M in qualified pipeline, and closed >$1M in net-new business with our portfolio companies. Exciting progress... and we’re just getting started! 

It’s important to highlight that our team coaches founding teams on how to execute in the same way we do to ensure the team can scale after GAP engagements. Founders use our playbooks and initial momentum to put their team on the path to scale for long-term growth. 

What’s your advice to AE’s who want to get into venture capital or angel investing?

Similar to sales, you have to get out there and meet with as many people in the industry as you can. Assuming you’re an AE at an earlier-stage company, think about the steps you took to land a job at a startup. Now think about taking that same process and digging even deeper to find a role in a very small industry. 

One thing that has been valuable throughout my career — and has certainly helped me at Unusual — is sharing my domain expertise and experience with VCs. Many are trying to find the next best company or help their companies build GTM functions. I’ve built some great relationships with folks by being a resource and adding value in certain areas. 

The guidance and collaboration with VCs throughout my career has helped me identify how to map my more tactical efforts to the key elements that matter most at the Investor/Board level:

  • Team

  • Product

  • Traction 

  • Market (where they can sell today to hit traction milestone and TAM)

Using my experience as a salesperson and learning how VCs evaluate investments and pitch to founders, I’ve noticed a lot of parallels between sales and venture. 

Pitching a firm is a lot like sales, but few firms have people with a sales background to help. Investors can benefit from sales input to refine the positioning, pitch, and articulating the firm’s unique and comparative differentiators.

Since making the shift to a remote-first culture, what’s been the best source for deal flow in 2020 so far? Has anything changed or is it still status quo? 

I ran this by Rachel Star and Jordan Segall on our investment team and here's what they had to say: 

“Despite the remote nature of our work currently, the general sources of deals have remained the same. Generally speaking though — I think people are more amenable to cold outreach because hoping on a Zoom is much less taxing than an in person meeting.” - Rachel Star, Senior Associate, Consumer Investment Team

“We haven't fundamentally changed our sourcing strategy since being remote, other than taking all of our meetings on Zoom! Since we are seed stage focused, it has always been important for us to try to engage and assist entrepreneurs as early as possible, even when the idea is just in their head. Perhaps before remote we would compliment our strategy with some in-person conferences focused on specific thematic areas to meet founders, which is obviously not an option in a COVID-era. But, our focus on being a resource to potential founders even before they've decided to commit to starting a company has remained unchanged." - Jordan Segall, Associate, Enterprise Investment Team

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You’ve written about the importance of ICPs (Ideal Customer Profiles) when it comes to scaling revenue orgs. What was your inspiration behind this, and how does this tie into your work helping portco’s at Unusual?

Great question — it seems like a silly thing to write so much about, but every single company has a gap in understanding their customer. From a B2B sales perspective, knowing who my ideal customer is helps me focus my time on seeking patterns and signals to qualify quality deals vs. wasting time on prospects unlikely to ever buy. That said, the way Product teams can make better decisions on what they’re building is knowing how, why, and what the customer needs from having a clear understanding of who they are. 

This is also relevant for finding PMF at Consumer companies as well — Unusual Partner Sarah Leary created this awesome exercise for Consumer companies, and Unusual Partner Andy Johns points out that your target customer “must be almost comically narrow to the point where you may be misunderstood for such a narrow focus.” 

Now, this may sound like a “startup problem,” but I can assure you that companies of all sizes hit a wall at some point. Examples include high churn, lack of pipeline growth, a growing list of customer demands that don’t fit the current product scope, expensive sales reps taking too long to ramp, etc. We recently met with a founder of a very successful startup who said, “I wish I knew who my customer was way earlier on — I wasted almost two years by not figuring this out at the beginning.”

More often than most think, companies of all sizes (seed stage to publicly traded) hire an outside sales consultant who rallies executive stakeholders at a company to conduct an exercise on topics related to  better identifying the company’s customer. Although this seems like a basic exercise, this can take teams days to come to an agreement, and 6-12 months to get employees up to speed on the topics discussed in those meetings — not to mention can cost companies a pretty penny to hire  the outside consultant to begin with. If you look at the landing pages of B2B SaaS tools, most use the same exact language — it’s not a coincidence.  Whether you’re hiring your first VP of Sales, or you’re discussing your traction metrics with the board, you must be able to articulate the information below to make sure the team is performant, but to get the rest of the organization to rally behind serving your customers:

“Why do people buy from you? What are the urgent use cases people want to solve?”

“Who buys from you? Who are the Buyers? What about the users?” 

“What are your differentiators? Who else can solve this problem?”

“What are the main three use cases that make up 80%+ of your revenue?” 

What is the perfect Enterprise sales tech stack in 2021?

There are lots of other tools out there, but I think you can accomplish a lot with this stack to start. (Here’s an image of the stack that I typically advise teams to consider during engagements) 

  • Apollo - find your target prospects and find their emails quickly

  • Datafox - find more target companies based on very specific inputs

  • Outreach - the best engine for prospecting to your target personas

  • Sales Navigator - find the specifics around your customers and prospects

  • Builtwith/HG Data - understand the technographics of your prospects and if they are a strong fit for your company

  • CRM (preferably Salesforce - it’s still the best option!) - a necessary evil to keep track of the “facts” about your customers and deals you’re pursuing

  • Chorus - use this to archive the key topics of conversation, but also a way to share with your team the specifics around a topic like, “This is what our ideal customer is looking for and here is an example.” 

  • Depending on your target audience, you can find prospects in Slack Groups, GitHub, Twitter, etc. Once you find where your prospects live and understand their world, you can have a value-added exchange and conversation with your ideal customers. 

  • Last but not least, teams with scaling teams need Orum and once your team has Sales Engineers on-board, Vivun is a must! 

The year is 2025. Will sales teams be “automated”? Is this a trend that’s emerging at all, or wishful thinking?

There are parts of sales that should and will be automated.

Transactional deals (like buying a $50/seat license) will become more automated, but the best companies will prevail by talking with their customers and knowing the specifics of their requirements in order to make changes on the fly like a world-class Engineering team. 

Superhuman is an example of a successful transaction without salespeople, but their onboarding process is very similar to how salespeople conduct discovery and map to the needs of their purchasers. They use such inputs to influence where they go next. 

Multi-million dollar transactions require cross-functional collaboration, a clear understanding of navigating organizational politics (external), and how to be a value-added resource. 

True “strategic” deals require so much manual effort that the only automation we should expect is improving the data and intelligence reps can acquire and use to drive deals forward versus being replaced. 

What are some observations you’ve noticed when working with founders and how sales could improve? 

Most founding teams are at one extreme or the other when it comes to sales process: they either have too much process or no process at all. That said, all should start with the basics of the topics below, but few formally go through this exercise until pipeline is looking a little scarce:

  • Specifics on who the hypothetical customers are, with market proof (outside of personal networks) to prove this 

  • Choosing an intended sales/GTM motion (PLG, Bottoms-Up, Top-down)

  • Conducting outreach to your prospective beta customers

  • Build qualifying data points they can use to signal the right prospects

  • Identify the “five critical questions” you need answered on every first discovery call across the technical use case, business use case, and what’s in it for them

If you’re in sales and are considering going to a very early stage startup, show founders you know how to do all of the above in order to help them achieve their fundraising milestones.

Thank you for your time and thoughts, Dakota. We look forward to the continued success of you and Unusual Ventures!

Deal News 10/10-10/16


  • Twentyeight Health raises $5,100,000 led by Third Prime | Twentyeight Health offers telemedicine services for women that aims to increase access to healthcare services.

  • Lassogen raises $4,500,000 led by Playground Global | Lassogen is a biotechnology company exploring lasso peptides as a way to develop new medicines.

  • FingerprintJS raises $4,000,000 led by Nexus Venture Partners | Browser Fingerprinting API

  • Profitboss raises $3,500,000 led by Redpoint | Profitboss powers direct online ordering for restaurants through their website.

  • Grata raises $3,200,000 led by Bling Capital | Grata is a business-to-business search engine for finding and targeting private companies.

  • Coa raises $3,000,000 led by Crosslink Capital | Coa is a Mental Fitness company.

  • SunDensity raises $2,500,000 led by Clean Energy Ventures | SunDensity provides photonic solar conversion products and services.

  • Caliber raises $2,200,000 led by Trinity Ventures | Caliber is the future of fitness coaching.

  • Boardroom Labs raises $2,157,500 led by Standard Crypto | Boardroom is an integrated governance management platform improving distributed decisionmaking across crypto networks

  • NowPay raises $2,100,000 led by Endure Capital, Foundation Ventures | NowPay improves the financial-wellness of corporate employees.

  • The Juggernaut raises $2,000,000 led by Precursor Ventures | The Juggernaut is a digital media publication focusing on South Asian stories.

  • Osmind raises $2,000,000 led by General Catalyst | Osmind builds a care platform for treatment-resistant mental health to accelerate drug development.

  • Hamama raises $2,000,000 | The fail-proof way for anyone, anywhere to grow nutritious microgreens at home year-round.

  • Memberstack raises $2,000,000 led by Gradient Ventures | Turn websites into members-only sites, dashboards, web apps, and intranets.

  • Genemod raises $1,700,000 led by | Genemod is a unified platform for life scientists to collaborate and streamline day-to-day operations in the research lab.

  • Glimpse raises $1,503,120 led by Origin Ventures | Glimpse provides product placement opportunities for short-term rental hosts.

  • kegg raises $1,500,000 | Kegg is a two-in-one device that combines fertility tracking with pelvic floor exercising.

Series A

  • RayzeBio raises $45,000,000 led by venBio Partners, Versant Ventures | RayzeBio is focused on improving outcomes for people with cancer by harnessing the power of targeted radioisotopes.

  • Argyle raises $20,000,000 led by Bain Capital Ventures | Argyle provides a consumer-controlled, software gateway to employment records.

  • Vivun raises $18,000,000 led by Accel | Vivun offers an AI-powered software for Presales, designed to transform how B2B technology companies go to market.

  • PassiveLogic raises $16,000,000 led by Addition, Keyframe Capital Partners | PassiveLogic - the world's first fully autonomous buildings platform.

  • actnano raises $12,000,000 led by Emerald Technology Ventures | actnano specializes in smart coating solutions that make electronics water-resistant.

  • Podium Education raises $12,000,000 led by Sid Krommenhoek, Zander Rafael | Podium Education helps colleges and universities add in-demand tech skills to undergraduate majors.

  • River raises $10,400,000 | River is a content discovery platform that pulls stories and content from across the entire internet.

  • JAXJOX raises $10,000,000 led by Dowgate Capital, Nigel Wray | JAXJOX introduces InteractiveStudio, a fitness platform that combines connected strength-training equipment with live and on-demand content.

  • Playbook raises $9,300,000 | Playbook is a mobile marketplace where instructors in health, fitness, and athletics upload their content and generate significant revenue.

  • Sanity raises $9,300,000 led by Threshold | Sanity is a software platform designed for delivering structured content to products and devices.

  • acceldata raises $8,500,000 led by Sorenson Ventures | Acceldata is a data observability platform for enterprise analytics and AI.

  • Findem raises $7,300,000 led by Wing Venture Capital | Findem is a People Intelligence platform that helps companies build more engaged, diverse teams and close their talent gaps faster.

  • Tiltify raises $6,500,000 led by Pace Capital | Tiltify is first crowdfunding site designed to turn your live streams into a charity fundraiser.

  • Qcode raises $6,400,000 led by Sonos | Qcode is an audio production studio.

  • Covetool raises $5,700,000 led by Mucker Capital | Cove.tool is a B2B SaaS company that helps make buildings energy efficient while saving on construction cost

  • Trade Roots raises $4,900,000 led by Greg Wirsen | Trade Roots is an adult-use craft cannabis company.

  • Aumni raises $3,000,000 | Aumni offers a solution that top VC firms use for a competitive edge and operational efficiency.

  • Immerse raises $1,500,000 led by Eagle Venture Fund | Transforming the way English is taught and learned using virtual reality

Series B

  • Cedilla Therapeutics raises $57,600,000 led by Boxer Capital, Casdin Capital | Cedilla Therapeutics is a biotechnology company that develops targeted small molecules for the treatment of cancer and other diseases.

  • Alkira raises $54,000,000 led by Koch Disruptive Technologies | Alkira Network is a developer of a network cloud that allows businesses to build and position multi-cloud network-as-a-service in minutes.

  • deepwatch raises $53,000,000 led by Goldman Sachs | Deepwatch is a cybersecurity company advancing SOC operations through its data-driven SecOps platform.

  • Menlo Micro raises $44,000,000 led by 40 North Ventures | Menlo Micro is a developer of an electromechanical switch technology used to offer products from battery chargers to electric vehicles.

  • Extend raises $40,000,000 led by Meritech Capital Partners | Extend provides extended warranties as a service to merchants and reinvents the broken customer experience associated with them.

  • Whisper raises $35,000,000 led by Quiet Capital | Whisper is an artificial intelligence platform that uses deep learning in hearing aids to amplify only the voices and sounds of interest.

  • Cribl raises $35,000,000 led by Sequoia Capital | Cribl is an observability pipeline company that provides administrators control over their data in motion.

  • Kasa Living raises $30,000,000 led by Ribbit Capital | Kasa Living is a hospitality company that offers flexible accommodations for business and leisure travelers.

  • Instylla raises $25,400,000 led by Catalyst Health Ventures, Excelestar Ventures | Instylla’s focus is to leverage hydrogel technology.

  • FOSSA raises $23,200,000 led by Bain Capital Ventures, Canvas Ventures, Costanoa Ventures | FOSSA provides a platform that helps enterprises manage and maximize open-source use at scale.

  • Finexio raises $23,000,000 led by Medalist Partners | Finexio offers a smart B2B payment network system for buyers and sellers which links payment rails to automate commercial payments.

  • Sonrai Security raises $20,000,000 led by Menlo Ventures | Sonrai Security delivers a security platform focused on identity and data governance inside AWS, Azure, Google Cloud, and Kubernetes.

  • Matroid raises $20,000,000 led by Energize Ventures | Matroid provides a studio to create, combine, and use computer vision detectors, without programming.

  • Yotascale raises $13,000,000 led by Felicis Ventures | Next-Generation Cloud Cost Management.

Series C

  • Snapdocs raises $60,000,000 led by Y Combinator, Continuity Fund | Snapdocs is a mortgage technology company that helps real estate participants closing work together through integration and automation.

  • M1 Finance raises $45,000,000 led by Left Lane Capital | M1 Finance specializes in financial technology, investing, investments, fintech, automation.

  • Armory raises $40,000,000 led by B Capital Group | Armory is an enterprise software company commercializing the open-source continuous delivery platform, Spinnaker.

  • Vineti raises $33,000,000 led by Cardinal Health | Vineti is a commercial cloud-based platform that expands patient access to life-saving cells and gene therapies.

Series D

  • Plenty raises $140,000,000 led by SoftBank Vision Fund | Plenty is a vertical farming company that brings fresh, pesticide-free produce to customers.

  • Augury raises $55,000,000 led by Qumra Capital | Augury is a developer of an AI platform providing insights regarding the health and performance of the machines used by customers.

Series E

  • Getaround raises $140,000,000 led by PeopleFund | Getaround is a peer-to-peer car sharing marketplace that enables car owners to rent out their cars.

  • 98point6 raises $118,000,000 led by Activant Capital, L Catterton | 98point6 is a digital primary care service that provides personalized consultation, diagnosis, and treatment to patients.

Sources: Crunchbase, LinkedIn, Twitter

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