From Burnout to Breakthrough
When Toby Fox-Mason launched his agency, Ashgrove AI, he envisioned Upwork as a steady client acquisition channel. The platform was booming with demand for marketing and automation services, but reality quickly proved harsher than expected.
For weeks, Toby spent two hours every day manually scraping jobs, scrolling through dozens of irrelevant postings. Because of time zone differences, he was usually 20 hours late to the most promising opportunities. By the time he clicked in, there were already 20–30 proposals submitted.
His output averaged just half a bid per day. The results were negligible.
I felt like I was spinning my wheels, watching opportunities slip away, and beginning to think Upwork was too saturated.
Exhaustion set in. Instead of spending his energy on revenue-generating work, he was stuck in low-leverage admin tasks. Burnout crept closer each day, and the thought of leaving Upwork altogether became tempting.
The Turning Point
Despite his frustration, Toby refused to quit. He knew there had to be a better way to work the platform. That’s when he discovered GigRadar.
At first, his perfectionist tendencies held him back. In his very first week with the tool, he spent days perfecting scanners, researching keywords, and rewriting proposal templates. He didn’t send a single proposal.
Perfectionism equals paralysis. I thought I was being smart by optimizing, but I was just stuck.
The realization was painful but liberating: he had to abandon the idea of the “perfect” campaign. Instead, he needed to launch messy, collect data, and improve later. GigRadar gave him the platform to do exactly that.
What made the difference was more than just automation. GigRadar provided:
- Real-time Slack alerts for new job postings, eliminating wasted hours.
- Scanners that pulled in opportunities across time zones, ensuring Toby was early, not late.
- Dashboards to track meaningful metrics like cost per reply instead of vanity stats.
This wasn’t about saving time, it was about transforming Upwork into a predictable, data-driven business system.
Scaling with Volume and Simplicity
Once Toby embraced GigRadar fully, the results came fast. In his first 30 days, he sent 288 proposals, more than he’d managed in the prior months combined. Out of those, he received 60 replies and closed 5 contracts.
The upfront value of those contracts totaled $8,600, all from an initial $1,000 Connects investment. That’s an 8.6x ROI in just 45 days.
The irony? He didn’t win by crafting elaborate, carefully polished proposals. His winning formula was astonishingly simple:
“Hey, I recently completed a similar project [add brief detail]. Do you mind if I send you a breakdown of the process?”
That was it, two sentences only. No overcomplicated storytelling, no walls of text. Just a low-commitment, value-driven offer to share expertise.
People want to over-optimize. The truth is, you just need to be specific without overwhelming detail, offer value, and ask a simple question.
This stripped-down approach produced a 25% reply rate, 5 times higher than what most agencies achieve on Upwork.
Data, Not Guesswork
Toby credits much of his turnaround to a mental shift inspired by the law of large numbers.
Instead of obsessing over single proposals, he looked at the averages. Ten proposals meant randomness; a hundred meant trends; five hundred meant a business model. GigRadar’s dashboards gave him the clarity to see these patterns emerge.
Men lie, women lie, numbers don’t. Once you send enough proposals, the averages tell you the truth.
He tracked the one metric that mattered most: cost per reply. With GigRadar, he could see exactly how much Connects investment was required to generate replies, and from there, how many replies converted to contracts.
The system turned Upwork into something he could finally predict and plan around, instead of a chaotic lottery.
Refinement Without Overhauls
Of course, not every experiment worked. Toby learned the hard way that even small tweaks could backfire. At one point, he added a short “three-step breakdown” to his two-sentence pitch. The result: his reply rate plummeted from 15% to 7%.
One tiny change tanked my results. That’s why you need to test one thing at a time.
Instead of panicking, Toby leaned on GigRadar’s monitoring. Real-time alerts and daily metrics allowed him to see when numbers dipped, but also gave him the confidence not to overreact. He refined slowly, kept volume steady, and optimized scanners for higher-value projects.
By the second month, he was winning larger contracts without sacrificing reply rates or proposal volume.
Beyond Contracts: The Hidden Benefits
The tangible results, contracts, ROI, reply rates, were impressive. But Toby insists the hidden benefits were just as transformative.
- Time freedom: He went from 2 hours of scraping per day to focusing on sales calls and delivery.
- Algorithm boost: Consistent activity improved his ranking within Upwork search.
- Keyword optimization: GigRadar surfaced powerful keywords that boosted his visibility even further.
- Confidence: Instead of wondering if Upwork was worth it, he knew exactly how much input produced how much output.
- Strategic growth: With his client pipeline predictable, Toby could finally launch new initiatives like a YouTube channel.
GigRadar gave me not just economic benefits, but psychological benefits. I wake up knowing there’s AI working for me, giving me consistent outreach.
For the first time since founding his agency, Toby felt in control.
Lessons for Other Agencies
Looking back, Toby sees where most agencies go wrong on Upwork:
- They underinvest, spending $50/month on Connects and expecting miracles.
- They panic too early, abandoning campaigns before meaningful data appears.
- They change too many things at once, never knowing what caused success or failure.
- They chase perfectionism, writing long-winded proposals instead of getting volume.
His formula for success is straightforward:
- Launch messy, perfect later.
- Send at least 50 bids in week one.
- Track cost per reply, not vanity metrics.
- Budget like a real business — $800+/month on Connects.
- Tweak one element at a time.
It’s not glamorous, but it’s predictable, and that makes all the difference.
A System, Not a Gamble
In just 45 days, Toby Fox-Mason transformed Ashgrove AI’s Upwork strategy:
- From half a bid per day → 288 proposals in a month.
- From manual scraping → 24/7 automation.
- From doubt and burnout → confidence and consistency.
- From $1,000 invested → $8,600 in contracts.
From two hours scraping jobs to having an automated system 24/7. GigRadar gave me time freedom and a predictable pipeline I can trust.
For agencies struggling to stand out in Upwork’s crowded marketplace, Toby’s journey shows the path forward: stop guessing, stop perfecting, and start scaling with automation and data.
👉 Ready to transform your Upwork results? Book a demo with GigRadar today and see how predictable client acquisition can change your business.
